peacetime not Dominion war timeframe. In TNG many main characters spoke of "in my class" acquaintences, which would seem to me to indicate a fairly small size for Starfleet academy. Was Gary Mitchel and Kirk both ending up on the same ship a simple coincidence made possible by a small 23rd century fleet size?
I went to a division III university and I can't say I felt great class loyalty in a vein similar to one expereinces with a high school graduating class.
Also what is the rate of retirement from Starfleet? Both Kirk and McCoy apparently retired for a brief time despite being more or less "lifers". You can't create more officiers than there are positions for obviously.
How long do people remain in Starfleet? Mr. Adventure seemed in awe of Uhura's twenty year space veteran status. Yet as a counterpoint most of the Reliant's bridge crew seemed to be well seasoned vets with rank lower than that of Commander Checkov's.
Finally the battle of Wolf 359 was both a massive loss of life and one that could be made good in a year? What does that indicate as a picture of mid 2360's fleet strength?
The Federation is huge, but how large is Starfleet? How big does it really need to be during peacetime?