Really greatful for all the good tips and information in your responses. A couple of things I should clarify.
I do not currently need to maintain 'the hay field' which makes up about 7acres of the 15acres. We have a very experienced rancher next door who cuts and bales this field each year for us, and takes 90% of the hay for payment. I chose to include the full acreage because I can't predict the future. This arrangement could come to an end, or we may decide on a new use for this space.
Our budget is 30k or less. I plan to purhcase some used additional impliments when they pop up. For now it would likely be just a rear blade and a small tiller.
I think everyone who's responded so far has suggested I go with the larger L2501 or CK2610. I feel most comfortable with these options but my only issue with these is that they're pretty wide for tilling our small garden rows. I'm thinking maybe we could run a narrow tiller (3 feet?) that fit between the rear wheels and run the wheels in the paths. Is this method common?
Those two tractors I mentioned are very similarly priced locally, but any addons like rear remotes and implements are 1/3rd the price from Kioti (can't figure out why that would be...). I'm wondering about quality and resale value. Anyone have any comments on differences between Kubota and Kioti?
Thanks again for all the thoughts. I get the feeling I'll be asking more questions here in the years to come...
If you want to make hay someday, you will want a noticeably larger tractor than any of the ones you listed. However, unless you get some very used/abused and inexpensive old hay equipment and fix it up, you will spend a fortune on equipment to hay only 7 acres. A small square baler doesn't take that much power to run (25-30 PTO HP or so) but you need a tractor that weighs more than the baler does (3000-4000 pounds) so the baler won't push you around or shake you to death. Round balers take more power, usually a tractor to run a normal-sized round baler starts at 75 engine HP and goes up from there.
Generally tractor cultivation is done by straddling rows and using a shank/shovel/sweep type cultivator rather than spacing the rows so widely that you drive between them and use a rototiller. Traditionally, you straddled two rows and your left tires ran to the left of the left row you straddled, and your right tires ran to the right of the right row you were straddling, and wheel centerlines were half the distance of the row spacing (e.g. 60" centerlines for 30" row spacings.) If you had a narrower tractor or wanted very wide row spacings, you would straddle one row and your row spacing was your wheel centerline spacing, you would put your right wheels right of the row and your left wheels left of the row you were straddling.
However, you will want a tractor with quite a bit of ground clearance to cultivate as you are driving over the top of your plants. You also need to make sure that the wheel spacings available on the tractor you intend to get, your row spacing you intend to use, and what row spacings your cultivator can handle are all compatible. A modern compact may give some difficulty here as the front wheel spacing may not be adjustable and the front axle clearance may or may not be sufficient to straddle the rows without knocking over your plants too badly. A smaller old ag tractor would be a lot better than a modern compact of roughly the same HP for cultivating, due to the much higher ground clearance. I do successfully use a tractor to cultivate my 1/3 acre garden but it's a full sized utility tractor with over a foot and a half of ground clearance and has a lot of adjustment in front and rear axle wheel spacing. I use it with an old two-row 3 point mount row crop cultivator with a toolbar and trailing mounting rigs so the shanks are offset in the front-to-back direction relative to each other, so they don't plug up like they do on the type of cultivator Jeff9366 posted. The angle-iron cultivator with a piece of angle iron across the rear (not like the one posted which does not) is better, you can drill holes there to mount shanks as well.
The other tasks you mention can be done with about any size of tractor as you can size a blade or bucketful of material to the size of the tractor you get. You can drive a very heavy tractor on soft ground just fine without rutting, you would just need to use wide flotation tires with nonaggressive tread to do so. However, those tires also give less traction than narrower, more aggressive tires, so it's a tradeoff.