Hi Teddy,
My wife and I are into month number 15 of our journey back to country life. Here's what we did, and why. Better still I can give preliminary results.
Prior to moving back to the country while we were looking for the right piece of ground (minimum 10 acres, max of 20, rolling hill type profile, with a minimum of 3 tillable acres, but mostly wooded) I loaded up on what I call cross over equipment. I bought a Scythe, because I knew a bush hog, rough cut mower, etc would not be in the budget. I also bought a very used riding mower and was able to use it on our place in the city for a couple years. (yep it took a while to find what we both wanted) Our self propelled mower, and medium size (6 hp) tiller, weed eater with blade and string head all made the transition without issue.
The riding mower was marginally useful on the yard area, and less than worthless for all other activities you'd want one for. We ended up buying a Cub Cadet Garden Tractor to mow with, and pull the garden wagon, as well as "ATV-type" ground working equipment. I recommend a full sized tractor if you are going to have much more than 5 acres of open ground.
The self propelled walk behind mower has proven to be very versatile, and very useful in the yard, and in the woods maintaining some of the easily accessed trails, and parts of the edge of the woods. Keep it, lube up the deck height adjusters and keep the blade sharp!!
The tiller is a Troy-Built, standard forward rotating tine design. If you get one, buy the weight kit!! I borrowed a counter rotating tine model to help break up the hard packed soil in the area we chose for the primary vegetable garden. They are ok, but very slow to work with.
The Scythe has actually proven to be a better investment than a weed eater. There have many times that the weed eater just could not get the job done, even with the blade installed. The Scythe when properly sharpened has easily out performed the weed-eater. And yes the string trimmer in question is actually two. A Troy Built and a Poulan both with 31cc motors, split shaft, gear driven heads.
Our plans for future equipment do not include a tractor at this time. Eventually we will get one, but do not have the need for one at this time. An ATV and further impliments to be pulled by one are the next on our list.
This is a great adventure, I hope you enjoy your journey back as much as we have.