Good thoughts and I don't disagree with all of it.
What I'm suggesting is you need to take a look around the league. Who is the team that will be better than the Spits? Go east and Barrie for sure but who in the west? Soo will be rebuilding along with Saginaw. London is just London so they will be in it. Erie looks close to Windsor. Kitchener will be rebuilding along with Flint. Guelph is a year or 2 away. Not sure where Owen Sound will fall. The only team that will be interesting and may be strong is Sarnia. So why not be the best team in a down year? If they fold this year the Spits will be 3 or 4 years away again. You can add another 3 or 4 years to no playoff wins. There is no reason at this point for this management group to not go for it - I mean they want to sell so folding should not be in the cards.
And the best reason of all - I'm too old to wait around 3 or 4 years to see a winner.
If the past seasons had went as many suggested they would have been set up for three or four years. They didn't, it's too late now but while they aren't contenders IMO they're not far of if they were to take action now. I don't think we would be waiting three to four years to see another contender. They could contend in two years if they acted now/this season.
As you've said, their draft picks are decent and I agree they are for a team looking to make a pick in every round for the next five drafts. With that base of picks moving out any 02s that have good to very good value would double their picks and bring back decent to good 04s. If they could get anymore 03s and/or 04s that show promise to report along with some luck in the upcoming draft they could be a solid team next year with assets to back themselves up while not having to go into full tank mode.
Cuylle and Foudy would return a couple of 2nds and a decent 04 each, especially they get off to a good start and show they are what people thought they would be. Both have done relatively well in the AHL, they've grown their games and shown they can handle that type of pace. They should also be able to carry that back and take on leadership roles.
McDonald and Robinson could each bring back a couple of 3rds or so, maybe more, maybe a bit less depending on how their season's start. McDonald in particular has been bounced around this line up the last two years. Every time he showed promise it was right back to the fourth line.
I believe the OAs are already set for next year. They'll start with Medina in goal, Renwick on D and Maggio up front. A fair amount of high end assets went for them and right Maggio is a 4th line player on most teams, 3rd line on this team while Renwick is an unknown. 02s are our OAs next year and with the connections they aren't getting traded and even if they did the return would be pretty low barring some amazing seasons from them this year. That leaves McDonald and Robinson as the odd men out next year. They haven't been too happy under Letowski according to speculation around here so if that hasn't been fixed and Letowski returns that likely makes for a tough start to the season with roster already if things are still simmering.
If there was a chance to get a solid return for D'Amico Henault, not some mid/late round pick I would move them and backfill with a couple of cheaper options. If the value isn't there then keep them.
As for teams in the West in comparison to Windsor?
Erie is a couple of steps behind Windsor. Looking at their roster from last season they only have a couple of 02s/03s with any type of experience. On top of that they have a few 2nds between now and 2025 and not much else in the 3rd/4th rounds. They didn't sell as much as they should of and like Windsor they've been going through the motions the last couple of seasons. Both teams peaked in 2017 and both teams are behind where they should be in a rebuild. Windsor is further along.
Flint was building for 2020/21 and because of what went on they've missed their window. 2019/20 they tried to take an early, blew by Windsor along with many others but they were gearing up more for the season that never happened. Their roster will be somewhat depleted and inexperienced but in terms of picks they're right there with Windsor with Windsor having an extra 2nd I believe and Flint having more 3rds/4ths when combined. Windsor is likely ahead of Flint but depending on the OAs that they return Flint has a chance to make up some assets that would keep them going forward right in line with Windsor if Windsor stands pat again.
Guelph just went on a Memorial Cup run a couple of seasons ago and as I mentioned a number of times last year, the moves they made early put them right back into a similar position as Windsor last year. They have pretty much the same assets, a more experienced and deeper 02/03 group and are further along in development than Windsor. Are they a top tier contender? Not right now and if they wanted to move everything they have they could be closer than Windsor. The unfortunate thing for Guelph was that there were players at the deadline that blocked trades otherwise they would be much, much further ahead of Windsor right now instead of just three or four steps ahead. They have fewer holes than Windsor with similar assets and a slightly better roster.
Kitchener is in a tough spot. They have no 2nd round picks for the next three years, they went all in for 2019/20 and but came up short of assets to really go over the top. Most players they were likely counting on to recoup draft picks through trades in 2020/21 will be graduating with a couple hanging around for an OA year. They'll be going full rebuild but if they can get a few of their high end prospects to report that'll be here for another year or two, get enough back to recoup those 2nds they'll be in a better position than Windsor next year if Windsor stands pat this year. A lot of ifs but this year Windsor currently is further ahead than they are. Kitchener has had much better luck/results getting higher end kids to report than Windsor so while they won't be contending this year they'll be in the playoffs.
London, everyone's measuring stick. Windsor has a couple more draft picks, not many but London has the overall much better depth and size of their 02/03 draft classes with a number of 03 prospects waiting in the wings. Windsor has the pick advantage but one solid deal gives London the advantage. London far and away away the better roster starting with Brochu who will likely be one of the top goaltenders in the league. They have prospects and players that will bring in very good returns as well as others that will make an impact on their season. It's not even close.
Owen Sound is similar to Erie at the moment in terms of roster. They had an older roster that was probably built more for 2020/21 with a small group of 02s/03s. Their draft picks are close to Windsor with Windsor having a couple more 2nds/3rds/4ths combined, but not many. Advantage Windsor here. Owen Sound is probably two years away.
Saginaw is similar to Erie except they were going on a two year run, 2018/19 and 2019/20 with 2020/21 being their time to sell. They have a small 02/03 group that has any experience although if Lennox is on his game they'll have a solid asset there come the deadline. Their picks are thin and it'll be tough for them to do much. Advantage Windsor.
Sarnia is a step below Windsor in terms of roster and draft picks. Depending on they get back in OAs that could even things out a bit in both roster and picks. They don't have a lot of 02/03 depth on the back end and up front they are a bit thin but their 03 class is probably a bit ahead of Windsor while Johnston is probably the best of both teams for the 03s. They should be battling it out with Windsor much of the season but I would give Windsor a slight advantage.
SSM is like Sarnia except they are more on par with Windsor. Windsor has an extra pick or two maybe and a couple of more 02s on their roster but the quality of the 02s, outside of Foudy and Cuylle is probably advantage SSM. Like Sarnia it'll depend on their OA situation. They built for 2020/21 and while it shows looking at their 2019/20 roster they've also shown an ability to grow and pull from an every deepening prospect pool and have become consistently better at maintaining a competitive team from year to year. High end 02s, advantage Windsor, draft picks are a small advantage Windsor while their depth 02/03 players and potential OAs goes to SSM. I would rate them about even with any advantage going to whoever makes the moves to improve or not sell. SSM has not really sold off in about 6 or 7 years and if there had been a season this past season the expectation would have been to sell. Here's the thing, without selling they and Windsor are pretty even, if they sell even a couple of pieces they'll likely be ahead of Windsor by quite a stretch next year if Windsor were to stand pat.
So London and Guelph are ahead of Windsor, Sarnia and SSM are basically right there with Flint now too far behind depending on their luck with returning players. The remainder are a step or more behind Windsor at this point. Today I would rank them for playoffs, based on Letowski returning and Windsor doing nothing and the other teams having just a bit of luck with returning players.
1 London
2 SSM
3 Guelph
4 Sarnia
5 Windsor
6 Flint
7 Kitchener
8 Erie
9 Saginaw
10 Owen Sound
It's way too early to make any real predictions but simply basing it on who's returning from their 2019/20 rosters, draft capital available to deal, players available to be traded, teams ability to attract prospects, teams willingness to make deals and recent history and consistency of how the team has been run. The past is not always indicative of the future but more often than not when you have people who have been involved for any length of time ti can be telling of what to expect.
Windsor in 5th, I was guessing 6th before I took a closer look seems about right based on what I laid out. Can they take their division? Yes with some moves but London and Guelph are tops in the conference IMO. Even adding when Guelph is a better team and capable of matching Windsor on moves Windsor likely doesn't get beyond the 2nd round.
For Windsor to take the division SSM and Sarnia have to be looking to sell at least a couple of pieces or have no luck in returning OAs. Windsor needs to improve on Ladd as an OA D, Henault as well and have Robinson be here and take a big step all around and Sobolev be what most are hoping for. So one, preferably two top 2/4 D. Windsor also needs to hit on a top tier import up front along with McDonald showing he can be a top 6 forward and if Letowski is back, McDonald gets consistent playing time. They also need a 2nd line LW so D'Amico can play 3rd line LW with Zito and Maggio. Finally Medina needs to be a top 8 to 10 goaltender that can be consistent every night and Downey has to be ready to go at this level for 20 games or they need an experienced back up.
All of that, Guelph doesn't make too many moves and London, well they'll have to deal with London and yes this team can compete for the conference. It'll wipe out their draft capital and we'll be headed for another 3 to 4 years of scraping by to hopefully make the playoffs with only Johnston, McDonald and Robinson as moveable assets unless Medina would accept a deal in his OA year. I don't think even with those moves Windsor gets out of the conference and if they do I think whoever comes out of the East will be the best team in the league even before the playoffs or the trade deadline.
Even if Windsor were to sell I think they still finish 6th, maybe 7th if they have a rough patch but they'll have enough picks to go on a two year run if they have the p[layers to make that run with with next year being a year they tweak the roster a bit to finalize the core for the following year. They would get more value from McDonald and Robinson in deals this year than next unless those two have outstanding years.
Yes a run is possible and within the conference for two rounds of playoffs even realistic but does the cost of likely two rounds of playoffs outweigh the future benefit of selling for a multi year run in two years with next year being a very good year as well?