Hello gm1 welcome to the forum and a Happy New Year.
I have a New Holland TC29 basicly the TC Boomer version of the tractor that you are looking at. I also have the 9x3 manual tranny and opted for the model with the fully synchro tranny with live pto. Which would be my suggestion to you, not only does the fully synchro tranny make it much easier and safer to operate. But the live pto is safer, with less wear and tear on your equipment. Just curios as to why you are not considering 4x4? Unless your land is flat and dry all the time, that 4x4 can really come in handy on these compact Utility Tractors. Another thing you really might want to consider is a front loader. There is a 1001 uses for a loader. And the TC30 makes a great small loader tractor. But 4x4 is preferred. The TC30 is a great midsize compact tractor especially for what you are doing. I can't comment on the price as I have never priced a stripped down model. Also the a new TC29 with the synchro tranny and live pto isn't that much higher in price than a TC30.
As far as mowers are concerned I pull a 6ft rear discharge 3pt finish mower with no problems. But a 6ft brushhog is a little much for the 25 pto hp. A 5ft works much better. And once again with that type of weight hanging off the front end. 4x4 can really be handy. If you go with 2 wheel drive you are probably going to have to hang some exrtra weight off the front.
Good luck on your new tractor purchase.