The concept of going all in is flawed from the get go. For a team mid window, sure adding UFA's or good players near the end of their contract at the cost of mid-tier and some later picks can be ok, especially as it seems deadline prices have fallen a little in recent years, but in general the salary cap almost demands the opposite.
If you have good players that you need to move out for cap purposes, moving on from them, and making some tough decisions can actually help extend your window. Washington wasn't afraid to move on from Semin and Green, Pittsburgh traded away Staal and Fleury, even Tampa moved Bishop not long after a vezina, and these types of decisions actually helped enhance the overall liklihood of winning a cup, and were key pieces of the puzzle for Pittsburgh's and Washington's recent success.
The new NHL is about identifying your real core, making tough decisions on players outside that group that are good but not vital, and not being afraid of taking a step back if it gives you more chances. Sometimes, it comes down to deciding you want one more crack at it with a team that has an 18% chance or do you want to make some smart decisions that gives you 3-4 more years with a team that has say a 14% odds each year.
It's unfortunate that media will usually need things to talk about in the here and now, so any team that makes a conscious decision that they are Ok with being a little less competitive now in order to extend their overall window with their core gets talked about in taking a step back, but it's the best path to a win.
Tampa will face tough decisions, and there is a very good chance that they will not be as good a team next year if they lose the luxury of being able to put a player with the talent of Yanni Gourde playing on your 3rd line, but it won't turn them into a weak team, and they will get assets that they can use to restock and retool.