The 8N is a good older tractor. However there are much better choices at a similar price point. I grew up with an 8N and my parents replaced it 5 or so years ago with a newer (1978) Massey.
When looking at an older tractor I would look for one in good shape and has some features
PTO
Get independent (lever turns pto on and off no matter if your clutch is engauged or not) or live pto (you have a two stage clutch, push half way down stops transmission, all the way down stops transmission and pto)
Steering
Get power assist or full hydraulic steering. My father commented to me that the turning radius is much tighter with the Massey. My response was the the Massey had twice the turning radius of the 8N, however you did not have to fight the wheel to get it to turn, so it turned faster.
Safety
If you have hills I would make a Roll Bar (ROPS) a requirement. If you do not have hills, ROPS are a great idea for a beginner.
Transmission
The 8N has a stupid fast reverse. Makes it a pain to back up and do detail work.
Hitch
I would make sure that whatever you look at has a 3 point hitch (3pt). This eliminates many older John Deere, and Farmalls from the list.
Loaders
Loaders are nice to have, however they can be a pain to mow with, and make the tractor ungainly. I love having a loader, however it is a pain at times too. The loaders for 8N's are terrible. Make sure the loader uses double acting cylinders and has cylinders for the bucket.
Parts
The cost of parts are another factor I would keep in mind. Ford and Massey have the lowest aftermarket parts cost and the strongest parts support. This is due to the high volume of older fords (9N-8N, 600-901, 2000-4000) sold in america. The Massey 135 style is another excellent choice for parts costs and availability as well. If you use the tractor a 6K tractor will break. Parts costs can be significant over the life of a tractor.
Yes they look cool and are simple but for practical use, I’d get something newer. I would recommend a newer subcompact or compact used. With your budget it would have to be a little higher hours but still have a lot of life.
Higher hours mean more maintenance, also part costs for compact tractors can get crazy. This does not mean that the compacts will have more or less repairs than an older utility, but the cost of the repair for older utility tractors with good parts support such as Ford 2000-4000 or a Massey 135, will be significantly less. Also parts for some brands such as Montana, Satoh, Hinomoto and Mitsubishi can be harder to acquire.
My advice to you would be...... Go into debt or wait until you can do it right.
Getting it right is a subjective idea. You can achieve what the OP wants with an 8N. However for similar cost, if not slightly more, yet under budget can use easier to operate equipment that has the similar simplicity as the 8N. I know that I help a friend on a farm, he runs old 70's tractors. His neighbor runs brand new Case IH. The neighbor has gone bankrupt twice so far. Those nice new Case IH tractors and their debt must be "doing it right". I know when I am sweating buckets in the cab with the windows open I am envious of their A/C though.
You can get the work done you want to with an older tractor. The bang for the buck of an older utility tractor is great. However the operation of it is a much steeper learning curve. They are much harder to run, the more complex newer tractors with hydrostatic transmissions make operators look like experts with only a few hours of use. Geared utility tractors take 10-20 times more hours to gain proficiency at complex operations.
When my parents were looking to upgrade our requirements were:
Good condition
ROPS
Live or Independent PTO
Power Steering
Loader
We ended up picking up a Massey 20C with a loader, and ROPS / FOPS (falling Object Protection) Cab, and diesel engine. It is an evolution of the Massey 135, and parts are easy to come by. However the steering cylinder and orbital motor is unique and will be $$ if work is needed. We paid $4K for it. Father then blew the engine up (check oil before running it) so we rebuilt it. I have mowed grass, leveled a building pad for a pole barn, cleaned up and leveled were the old barn was, moved tons of brush, pulled fence posts, and done much more with it.