Welcome CM,
You'll get plenty of great advice here, so I'll zero in on a minor mistake I made.
I bought 10 acres, and since it was full of brush and briars, I bought a bush hog. After bush hogging it 1-2 times, no more brush! I wished I had bought a finishing mower instead. I am now using my bush hog as a finishing mower. If I keep the blade sharp, I it does fair, but it sure is slow.
If you plan to mow 6-8 times a year, a finish mower may work best, and will certainly do a better, faster job. They're faster because finish mowers are easier to pull than bush hogs, and generally 2 feet wider for a given tractor.
All the above depends on how much of your acreage you plan to mow, and how often, of course. If you plan to cut your land only 3-4 times a year, a bush hog will probably work better on the tall weeds and grass. WIth 38 acres, you may eventually need both implements.
