I almost hate to look at the transactions every day...which guy is now going on the DL? What recent callup who I just signed to fill a hole was today just sent back down?
BWB is - among other things - a game of scarcity. And the decisions you make to deal with scarce resources will often decide the fate of your season.
Scarce Resource #1: Available players
You're in a league with 15 other teams. If you need to reach into the free agent pool to fix your roster, you might find the pickings slim in various positions (try to pick up a new backup catcher or a 2nd closer...I dare you).
Scarce Resource #2: Cash
It's not a matter of just going out and finding whatever player you want...you need to have the cash to pay for it. You can help yourself out by continuing to win games (you earn money for each win) - but you may need to make decisions to cut/trade a high-priced player in return for multiple players to fill your roster spots.
Scarce Resource #3: Roster space
You have only 5 bench spots and 2 spot pitcher slots that lets you have subs when your regulars are hurt or not playing for some other reason...not much needs to be said there. On top of that, you need to be aware that you have limits on the number of players you can sign who make over 250. You have a 40-man roster...but only players who make 250 or less can take one of your minor league spots. This gets even tougher if you're using a cheap player in a key role. You may find that you have to put him back in the minors because no one else can be sent down.
And the 40-man roster is definitely a limit too. You may have your top prospects all lined up for future seasons, but if you need to sign a player to cover an injured starter, it may mean cutting a rising star.
I'm always hesitant to fill a roster spot with a DH-only player. That's one fewer fielding substitute you've got and can mean problems in some games. Ideally, I like to find a good hitter who can play multiple positions as my DH. Multi-position eligibilty on the bench is valuable too.
Scarce Resource #4: Room for injured players
You've got one IR spot that lets you stash a player for next season (you can't make him active again) and only 2 taxi squad spots to store players you don't want on your active roster (either they're injured or make too much money to go to the minors). So, it starts getting a bit dangerous if you're storing injured players on your bench or in the spot starter slots. You may be fine...until someone else gets hurt.
Once in awhile, I'm asked about increasing the number of taxi squad spots - or removing the 250-salary limit for minor leaguers. But, dealing with these scarcities is part of the game. It forces you to make roster decisions - maybe finally cutting a player who won't be back until August (or next season) - and helps keep the game competitive.