Depends on what their level is. (Q30 = 6* at your level???)
As far as I can tell, best case scenario is a player will stay even with stars as you advance (assuming normal training, no token buying power training) - i.e. if he's 5* now, a full season training/playing will get him to 6*, but then when you advance to the next level, he'd lose a star and be 5* again next season.
So, unless you hit on an exceptionally well-training player, you're just not really going to train someone up from 3* to 6*. Remember too that their training will slow down at each step up ... they train MUCH faster at 3* than the same player will when he hits 4*, etc.
On the other hand, every skill point adds about $10k to the players value ... so you might hold off selling fast trainers so as to get more return when you do sell them.
The market goes through fluctuations as well (seasonal and daily). The best time to sell is during the insanity of the first week of the season. You'll often get double the value of the player you're selling during that period. (It's also the worst time to buy players). But your players lose value when the new season starts, too, so holding them until then isn't necessarily a good idea either.
As a direct answer to your question, if I have the quality to star level equivalents correct for your level, if they were my players:
DL/DC, Q27, age 20, 2.2m 5 star??? If so, keep him. maybe even if he's 4* and you can get him to 5* by the end of the season
ST, Q23, age 19, 1.9m Train him every chance you get until his condition is 0 or he gets injured, apply all skill points, and sell
This assumes they aren't your starters or primary backups - you still need to win your league.
some other things to remember-
- keep a full or nearly full roster. Even if they aren't playing, they can be training (farming $ when you sell them)
- The fastest way to make $ is to buy FAs and resell them (drawback: need tokens to buy them)
- if your roster is full, you can stash new players for up to 7 days before you have to sign them
- always try to get versatile, multi-position players
- ideally you'll have two full squads of starters (5* and better), with the weaker squad playing league, and your stars playing CL & Cup
All of these strategies may change at higher levels. At level 4/5 I'm starting to keep more players for multiple seasons.


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