So after reading some of your posts...
Regarding the city from a player's perspective....
...it really doesnt ever make sense for us to get our hopes up about big name free agents signing. Ever.
And those who we do sign will be the B/C/D level guys. And those who do, aren't gonna do it for super cheap because they are already sacrificing with location.
So suddenly, it becomes pretty clear why JR has 'not dont crap to address our issues in the off-seasons' and why players like Jack Johnson might be making over $3 mil to come here.
Without good drafting or trades, the Pens would really suck...there is just no attraction for 'stars' to come there willingly.
If Crosby and Malkin weren't uncommonly loyal, would either be in this organization by choice?
By all accounts, the Penguins run a first class organization. Lemieux and Burkle have established a reputation for hiring good people who care about the players (even if they aren't always actually good at their jobs).
Players have a lot of amenities here, they're given more help when it comes to adjusting to the city than other teams give, etc. Sid and Geno care about winning, so as long as they can do that and get treated well, they'd be happy even if it was an even smaller market.
The only reason the Pens haven't been getting big free agents is because they haven't been in the market for one. They've always been near the cap ceiling since Sid and Geno signed their big deals. They've re-signed a bunch of other guys in years past to extensions. So there hasn't been a ton of wiggle room.
Put it this way: If the Pens suddenly had cap space and a need for John Tavares, they'd be a favorite to land him. No question. Their reputation for treating players well and their commitment to winning are two huge selling points when the dollars are just about even.
Edit to add: As for other teams in Pittsburgh, the Steelers are just like the Pens. Highly respected owners who spend to the max and don't have a lot of room to add flashy free agents because they tend to give out extensions and keep players around instead.
The Pirates are the opposite. Great facilities, cheap ownership with poor reputation. So high profile free agents aren't interested (and the Pirates aren't interested in them either). But the players who live here love the city. Andrew McCutchen was traded to San Francisco but kept his house here and has said he'll move back here when his career is done.