Steve C. was correct. I am not inclined to do mechanical work. I don't know how. Steve C. makes some good points from an economic point of view. But, I am intrigued with "pushing dirt around" and keeping the pasture bush-hogged. Blading the snow off the lane would be interesting also. I am not sure I can handle waiting for the grass to be baled twice a year.
You might want to think about being patient and hiring out the tractor work out for a year and, in the meantime, look around to become really familiar with what tractors are out there and what you can and will do with them. Study the maintenance issues and see how well they mesh with your inclinations and skills. You might find that you will feel comfortable with a good used tractor. I mean after-all, there are a lot of good, low hour tractors out there at significant savings over new.
Think about this. A good tractor should run at least three if not four or five thousand hours if properly maintained. I have seen some larger tractors with as many as 10,000 hours. More than likely, you will not be using your tractor maybe, 50 to 75 hours a year if that much for your 18 acres. With that said, I would look at buying a good used tractor in the 25 to 40hp range. With the money saved you can buy some equipment and a good used commercial mower which are great on hills.
By way of example, let me describe the set up for my 101 acres which I just maintain.
2002 4500 Mahindra 2WD. Has 42hp though some claim it is 45hp. Bought 5 years ago with 180 hours for 12,000 with FEL and 7 foot bush hog. Now has 360 hours which equals 36 hours per year. I know a lot of people push the 4WD but, the 2WD's have been used for a hundred years and they have done the job just fine. I am completely happy with mine.
Commercial Mowers - Presently a Ferris IS3000 because of the suspension. Bought with 396 hours for $3800.00. Number of hours in three years the two commercial mowers I have owned, 160 or 53 hours a year. This includes mowing some fields with this mower in early spring and mowing around fields and barns the rest of the year. Expected life span of a commercial mower is at least 2000 hours if maintained at all. I have seen or heard of some with more than 3500 hours that were well maintained.
Total amount of work done on the above other than normal maintenance - Rebuilt starter on Mahindra.
Other equipment includes Tiller, Scrape Blade and Box Scrape. Total Cost - $1550.00.
Total cost of equipment above - $17350.00.
Whatever way you go, good luck
Dave in NC