None of it really bothers me in the least. The answer for most owners is to join a league during the allocation draft and keep em for 20+ seasons.
What does bother me is owners that join new leagues, go through an allocation draft, essentially building the entire roster from scratch, playing 1 season, then quitting before season 2.
My whole love of this game comes from my long tenured teams....Dakota Blizzard in XFL which I've owned for 22 seasons since allocation....Great Falls Quicksilver in Quick and the Dead which I've owned 23 seasons since allocation and the Houston Gamblers in USFL which I've owned for 16 seasons and took then over in season 12 or 13 of that league.
The good and bad of those teams can all be praised or blamed on me completely.
But I've taken over crop teams in other leagues and turned them around from doormats to contenders in a season or 2. Any team can be made a winner within a season or 2 if you have a vision for your roster. Free agency, drafting and trades are all key elements into building a winning team if you have a plan or what direction to take.
The key (to me at least) is to constantly keep upgrading your talent when you take over a new roster....ignore the dead cap that can mount from doing this because in the end it's the depth and quality of the roster that needs to improve to play out your personal vision and game plan.
The last team I did that for was in a private league called TPM...I took over a 3rd season team that won 6 games in their 1st 2 seasons and completely overhauled the roster through trades and free agency plus my draft picks and made the Conference championship in my 1st season. It can be done but it takes a ton of work constantly trying to upgrade the roster through the off-season and into the first few weeks of the season to get players that fit your style of play.
Take Smirt for example, he knows what he needs to win and will over pay via trade to get the right players plus he will make subtle moves on the fringes that seem meaningless but the player is a piece to the puzzle that is his style.
The hardest part is developing your own style of play and honing your personal player weights to match them so you can find the right players to fit. Once that is done, the rest kinda falls in place with a little work.