How much money would you need for enough tractor to do those activities?
realistically.. your rake could be 2500$.. a mower could be 2500-7500 depending on make age, etc. you might luck out and find a sickle bar for less and just take forever and a day. the round bailer will eat your lunch.. I'd rarely ever found a good enough to use one for less than 4000$
hp.. i wouldn't hit this with less than 50hp.. in a ford platform.. i think a 4000, 4600, 4610, 5000 5600, 5610 ( II and s series ) the later 6610 and 7610s are large int he 80 and 90hp ranges.. a lil overkill and will price you out, even being 10-15ys used.
so.. that 50ish hp tractor is likely to set you back 4500-7500$
all in all.. 1 machine to do all is a hard press fit.
if I was doing it.. I'd get the ( 4600-5610 ) and then have another tractor.. this one can be an older chapy.. like a ford 00 series from 55-64.. preferably an 8xx or 9xx model.. this will make a good rake.
also keep in mind with no loader you won't be stacking bales.. you will be stuck with 3pt bale carrier.
a ford 00 series with a loader will move 4x5 rounds.. but 5x5 are getting abusive. your 00 with a loader will be up to 3500$ or more if minty.. less if worked hard. without loader.. 2000+
or you can get a laoder for your main unit, and figure another 2500-4000$ IE.. expect to pay 10k$ for the tractor and loader by itself.
and that's what I'd do.. 4600-5610 with laoder.. bailer, rake and mower... and then a smaller ford like a 8xx or 9xx to mow and do other duties.. like pull a wagon.
you could go square bailer and save a couple thou.. but do more overall work.. need a kicker style and a follow trailer.. or will be making more passes and need labor.
small scale hay is hard.
the 2nd tractor is GOOD to have. if you did get a 8xx or 9xx ( or heck.. ford 2xxx/3xxx ) in a pinch it may run the bailer in an emergency..
probably not what you wanted to hear.
up to 50ac is quite a bit to maintain.
if it was just a hobby setup.. I'd say the old ford 8xx/9xx, sickle bar mower, rake and square bailer and you would still be around 10-12k depending on if a loader was in there and how badly the stuff was beat up.
( hay bailers require maintenance. )