This is a rare event where reality doesn't jibe with what happens in OOTP, so I at least do what's best in the OOTP world.
My minor league teams win. No exceptions. Even if I have to put a couple of ringers on their rosters. Because...
- I don't just develop players in my minors. I develop staff. And from what I've seen at least, staff development seems entirely dependent on the win/loss record of the teams they're attached to.
- No-one learns anything when their team is 30-72 and morale is in the toilet.
Off topic, by 'ringers'... personally I like to take old, worn out players who I have a soft spot for and give them one last year, even in the sticks, where they go 23-4 and look like their peak again. I did that with one guy and he threw a perfect game in the deciding game of the championship series before retiring immediately afterwards.
Yeah, maybe 20 virtual spectators attended that game but I'll never forget it.