I'd sell the Yanmar on my own. I don't think I'd have a hard time getting what I want for it with all the attachments I'd let go with it. I'll probably keep the blade since it was really a touch big for the yanmar anyways and then use the money from the yanmar to get a bigger rotary cutter, disk, etc.
I'd still suggest keeping the Yanmar for the little tasks. I have the size tractor you're talking about getting. It's great for most stuff. But, I'd still like something smaller available for little stuff... and you've already got the attachments sized for it.
To narrow down your decision, it might be important to talk about features and proper "sizing" of implements for the jobs you want done. I say that because you can easily spend under $30k to get a tractor that will move a round bale.
Features:
Transmission choice:
Do you want Shuttle Shift, Hydrostatic, Power-Shuttle? This is worth mentioning because if you want HST, which is the best transmission choice for constant loader work, that will limit you to certain tractor categories. Shuttle will widen the range the most, and Power-Shuttle will be somewhere in-between Shuttle & HST.
Options & creature comforts:
Do you want a tractor that comes with a quick-detach loader, extendable 3-pt lift arms, telescoping stabilizer arms, deluxe seating, tilt steering, standard remotes, etc? Don't laugh, but once you get used to some of these things, you'll wonder what you ever did without them. My first tractor did not have extendable lift arms, or telescoping stabilizer arms for the lift-arms... boy what a difference it makes! So much easier to hook up & adjust your implements.
Cab consideration: You can get into a 45-60 hp CAB tractor, with most of the above options, that will lift a round bale, for under $30k. I absolutely love having a cab. I think everyone that has a cab loves having a cab! Don't overlook this option because it really changes your comfort and experience if you're spending long hours on your tractor.
Capabilities - Implement sizing: There seems to be a general rule that you need 5-7 HP at the PTO, per foot of implement. So, if you want to run a 6 ft BrushHog, you should have around 30 PTO-HP. If you want to run a small round baler, I think you need around 35-45 PTO-HP.
If your bales weigh 1000-1500lbs, then pretty much any tractor in the large CUT (compact utility tractor) segment will lift them. For most companies, these start at 40hp & up. So, you don't necessarily have to get a tractor like the 5055e, as that is in the "utility" segment and is a larger machine.
Here are machines in the "CUT" range that would work.
Kioti DS4510HS (45 hp, power-shuttle, no cab option)
Kioti DK40,45,50 (40,45,50 hp Shuttle & HST - this model is now discontinued because it was replaced by...)
Kioti NX4510,50,55,6010 (HST or Shuttle)
LS R4047 (outgoing) or LS XR4046
TYM T503 (shuttle or HST)
Mahindra 5010 (actually the same as the TYM T503)
Mahindra 5035
Massey 1648,1652 (HST) 1655 (shuttle), 1660 (power-shuttle) - these models are now replaced by...
Massey 1749,1754,1758,1759.
JD 4320,4520,4720 - now replaced by the 4044,4055,4066.
Kubota MX4700,5100 - replaced by new models, can't remember the numering
Kubota Grand L - 4240,4740,5240,5740 - now replaced by
Kubota Grand L - 4760 & up.
There's more, but those come to mind.
Up from that is the Utility tractors, which will not have HST, but will come with Shuttle or PS. I really don't know the models in this class by heart - I know the ones from LS and that's about it LOL
LS U5020,U5030,XU5065
JD 5055E
Good luck!