SteveC makes some excellent points. Tractors seem to be all designed so that every single thing you need to do to them requires the maximum force an average male human being can exert (perhaps I am exaggerating, but it feels that way). If you really dislike mechanical work, it will be a problem, because even the installation and removal of an implement (they are all heavy-even the small ones) requires some knowledge of leverage and often the application of a tool of some kind (in spite of manufacturer claims to the contrary). Plus, there are many things on a tractor that need to be inspected, tightened, lubricated, or otherwise fiddled with on a frequent enough basis that it's not practical to haul it or have it hauled to a dealer for every little thing. However, I must say that in spite of all the work, aggravation, and possible loss of body parts, becoming proficient in using and working on a clattering assemblage of diesel engine, hydraulic systems, and moving parts is a rewarding undertaking. I love it, and would never think of hiring someone to mow or plow, unless it was an emergency. .....I have stayed away from used tractors (though the big one I bought had 50 hours on it as a demonstrator) because I don't know how well they've been maintained, and I figure somebody got rid them for some reason, maybe just to trade up, but maybe not.
When I bought my first tractor, I was a total newbie, though I am a mechanical engineer by training, and have worked on cars and other mechanical things since I was a kid. In spite of that I never knew how much I liked diesel engines and hydraulics until I got a tractor. I say that if you can afford it, and are willing to learn at least rudimentary mechanical skills, go for it! Then you can put on your overalls, go to town, and not feel like an imposter.