Yes, get a FEL. It's so useful. Finding one later on is difficult and expensive.
Many dealers will pick up and deliver machines they sold. Usually for free within a certain radius, otherwise there's a charge. Ask the dealer.
If you can change the oil in a vehicle you can do the routine maintenance on a tractor. Some of the parts and quantities are larger but the concepts are the same. You can also rent trailers if you need to. My dealer's 240 miles away. In two years since I bought the tractor I've been there once, to pick up a used backhoe, using a trailer I rented. They delivered the tractor and implements I bought with it for a reasonable charge.
How steep are the places you want to take the tractor? I have very steep land. There's a lot of it that I wont take the tractor on. I avoid side hilling on grades over about 10%. I only go up and down those. There's one road with a roughly 30% section that I have to take in low range. On anything steep I'm in 4wd so there's braking on the front axle. But a modern 4wd CUT will do better on hills than the 8N. Make sure you get the dealer to bolt the adjustable rear wheels in the furthest out position for stability, and consider getting the tires filled with ballast to lower the center of gravity and increase stability.
The general rule of thumb for mowing is 5 hp per foot of mower width. But if you're not mowing thick tall grass you can get by with less.