I would also urge you to go with HST. I have a Utility (LS P7010) with 20 F/20R gear drive with shuttle shift(have to clutch to shift) and believe me, it will wear on your knees after a while. The P7010 was too large to handle tight working spots although I have used it a lot in the woods and never broke any thing (so far). You do have to be careful about going under low hanging limbs, not so much for the glass but for the roof and lights.
After a year or so of ownership of the P7010, I found that lots of places I needed to get to, I couldn't so I found a second tractor was needed. Thanks to a fellow TBN member, I found a used (slightly with 68 hours) Kubota
B26 TLB which is my go to tractor for almost all my work now. I put about 100 hours on my P 7010 the first year but have only put 56 on it in the last 6 years. I only use it for the extra heavy lifting and garden tilling with my 6 foot tiller which is a little too heavy for my
B26 to handle. I do use my backhoe quite a bit still, mostly digging up rocks or tree stumps, cleaning out drainage ditches etc. I have recouped my money for the entire TLB purchase in the 450+ hours that I have used it so far although YMMV depending on how much work you have for a back hoe. If you don't plan to do a lot of backhoe work, you might consider investing the money in a cab rather than a backhoe attachment. If available, a rented excavator will do a lot of work in a short time period and is much more maneuverable. I like the fact that an excavator can swing 360 degrees rather than the 85-90 left or right for a backhoe. This is very handy when cleaning out a ditch or pond where you need to get your spoils back away from the edge of work.
As for haying, DONT DO IT. Equipment cost is way too much for that limited amount of hay even if you put the entire 27 acres in hay and used a small square baler, you still couldn't justify the cost of the equipment plus you would need a much larger tractor than all your other chores requires.
I really don't have any favorite tractor brand but I would think that a 40-45 HP (PTO) would be way more than you would need to do any chore that you have listed. My brother in law uses a New Holland 2910 to pull a 6 foot bush hog, lift round bales 3 high plus do all the FEL work that he needs on his cattle operation. I don't see that HST robs a lot of HP from CUT tractors since most if not all have more power than they have traction anyway. 3-4 HP from engine is not a significant amount for most instances and they are robust enough to handle all the ground engaging tasks that you would have PLUS be way easier on the legs when doing FEL work or even tight work with a mower that may require slow forward and reverse actions to get in and out of tight spots.
I think that if you try the HST, you will like it much better than a gear drive even a power shuttle type. I had a Yanmar with power shift and while good, it was not even close to working with HST especially in tight conditions where inching forward and reverse was needed. At the time, I thought the power shift was greatest thing until I got my HST tractor.