tractors generally aren't throw away items, so you generally need something that is repairable. being able to repair it means you need to be able to get parts and/or service. in today's world, many parts can be mailed directly just as easy as picking them up at the dealer, but there is always that time when you may need advice on something. it's nice to be able to work face to face with someone rather than rely on a phone call. for simple parts is sure is nice being able to pick them up instantly.
in the state i live in, we have 3 massey dealers, and about a dozen jd dealers. i am fairly central in the state and all 3 massey dealers are around 50mi or less away, but for people in the northern part of the state they could be 150mi away. i didn't check, but maybe there are canadian dealers just across the border, but that gets into a border cross and customs issue too, so more hassles.
i can't say for the size comparison on the these tractors, but i'd go with the biggest you can work with. by biggest i mean weight and not power. i think i'd gladly swap a few horsepower for several hundred (or more) pounds of weight. i have a jd770 with a woods 7500 backhoe, and i have uprooted some amazing size stumps - most are far too big to lift after i rip all the roots out, and i have to roll them out of the hole. i often find the biggest enemy is weight. i find times where i will pull the tractor with the hoe before breaking the root. more power never hurt either.
i bought my tractor in 1998, and back then there wasn't a lot available for used. they were generally well worn by the time they were sold, so i ended up buying new. i went with the 770 over a larger one because by the time i stepped up to a 970 or 1070 and went to the bigger hoe, i was jumping from around 20k to closer to 30k for the tractor/loader/backhoe. it was more than i could chew off.
for what i do, the size is fine. i run a 4" hydraulic feed pto
chipper, 5' rotary mower, 5' loader, 5' backhoe, and it's generally the backhoe where i find myself wanting more power and size, but then again, even if i had a larger one, i'd just find something too big for that to do too. i think that's going to be the case with any backhoe -they won't do what a 100k excavator will, even though we want them to.