In theory, it's do-able, but in actual practice, who knows? Some things to consider:
Rabbits stress easily; rabbits that are new to you will need a "settling in" period before they are put into production. It's just good sense to hold off breeding them until they have been with you long enough for any parasite/disease problems to show up, anyway. So, you're adding at least a couple of weeks at the beginning of every "season" when you are feeding animals that are effectively unproductive.
Rabbits should be fully grown before they are bred, for most breeds, this means at least 6 months old. If they haven't been bred before, they may not start right away; it may take a bit before they get the idea. Does often make a total mess of their first litters; apparently, instinct only gets them so far. So, if you are buying young stock, it may take a while to get them going. Things might take off right away for you, or, I could easily see how you might get 6-month-olds in September, but it could be December before you have anything to put on the table. It's a crap shoot.
If someone is selling older animals that have already been in production for some time, there's a reason they are for sale. Does are at their peak for the first year or so, after that, their litter sizes decline a little each year. Most does are effectively sterile at 4 years of age, though some produce well at 6 years or even later - it seems to depend on the bloodline as much as anything. Some does are rotten mothers, some just never have more than a few babies in each litter (though they may be good for fostering extra kits from other, extra-large litters), some does are just beasts to handle or may be hard to get bred. Like I said, they are for sale for a reason; and the breeder may not be completely forthcoming as to what that reason is.