I think you can race your horses once or twice a month, if they’re successful. I give my horses a really long rest when they don’t run well, not to waste money on them 
which especially applies to 2yos (except for [color=blue]GCh. Susurro - I race him quite a lot, but he seems to like it… most of the time).
But the unsuccessful 2yos get a month of rest, then 2-3 weeks of training, then again a few days of rest and a race.
I used to breeze my horses a few days before the race if they had a longer rest, but it doesn’t always work well.
By the way, I searched for horses that were raced most frequently; some of them two or three times a month, 20-30 times a year, with a race record of more than 80 races in their lifetime; including [color=red]WCh. Toast of the Town, [color=blue]FFCh. Black Cherry, [color=blue]WCh. Drum Major, [color=red]ICh. Eternal Lady, [color=blue]ICh. Gilded Saint. Of my own, I have some mares which have between 50-60 starts in their lifetime, but only two were raced by me - [color=red]GCh. Embellished and [color=red]GCh. The Woman In Black (both raced 50 times, and are injury-free). So looks like you don’t have to wait 3 months or longer for another start…
The only reason to wait several months between races (assuming no injury) is for morale gain. If your horse gets farm rest (boarding or at home) between every race it might never need to go to the farm for a long break.
FWIW, I know the race (and training) system isn’t as realistic as I’d like - hoping to revamp this in the beta as well, but that will take quite some time, so don’t look for it for several months years.
Very interesting, just looked at Black Cherry’s race record, What an amazing record. Most of mine must be very low on morale I guess (over trained!!). All training schedules been changed and hopefully the trainer will keep his job 
No rush on fixing the training’s lack of realism… I’m not looking forward to finding a new training regime! Ha. That will certainly level the playing field again, though.
I should perhaps change mine, as it’s my worst year ever; with 41% OTB. The best year was 2017 with 63%. Maybe I just had better horses!
I’ve certainly struggled with the training and my winning percentage has declined dramatically 
I’ve even looked to purchase horses from other stables with better winning percentages just to peek at their training methods 
Been revamping a few lately so time will tell.
Sorry to awaken this thread from the dead, but I am really having trouble finding this (though I’m sure I’m probably just missing it)–What does a jockey mean when they say, “[insert horse name] could carry more weight in races” when doing workouts? I was guessing it had to do with jockey weight but I wasn’t sure–I also thought at one time we could see a jockey’s weight but now I can’t seem to see where I saw that or if I just imagined it…
Jockey weights can be found in the list of jockeys. Just go to Racing --> Jockey List.
As for the comment of “could carry more weight in races,” I wouldn’t worry too much about it. Mostly, it means what it says, that the horse can carry more weight than it currently carries. This isn’t a bad thing. Some races will add weight to try and level the playing field. If a horse can carry more weight, and more weight is added, it should still be able to compete without penalty.
Did a quick search and found this from Shanthi, “It’s regarding jockey weight. Nothing you can do, really, as weights get assigned based on what sort of race it is. (However, if you get comments to the effect that your horse can’t carry any weight, and s/he is a MSW, you might avoid handicap races where they’ll get assigned a higher weight based on their performance.)”
Thank you so much! This helps a lot! 
You’re welcome. Glad I could help. 