Nothing against the TC55, but something to consider would be an LS U5030 (LS builds much of the New Holland tractors now, the NH TC series is the older Shibaura builds, don't seem to be as reliable as the new LS builds). I think for around $27k, you'll get a brand new LS U5030, 55 HP tractor, 4x4, dual rear remotes, draft control, telescoping 3pt links & stabilizers, loader (lifts around 2700-2900 IIRC) with self leveling bucket. It will also come with a synchro-shuttle trans. It will also come with a 5 yr warranty.
If I could have gotten that in HST (or the u5020 @ 47 HP) in a cab, I would have gotten it over the Massey I just bought.
I've spent nearly a year & 200 trouble free hours on an LS (except for a headlight fuse) and they make a good, dependable product at a good price point.
Something to consider anyhow, especially over buying used.
By the way, the u5030 with loader & bucket would weigh in just under 6000 lbs. Like you, I have a 7000# rated 16' trailer. I've used it in a pinch for my tractors (weighing in around 5500) but as soon as I can afford it, I'll be upgrading to a heavier trailer.