I will try to help out on this. Depending on the height of the grass for the first cut, you should probably look at equipment to maintain the 5 acres after the first cut, as you probably figured out already. The tow behind self powered Swisher works well in an open field, get the bush hog model not the finish mower. The best would be to find a good used tractor with a PTO as already stated above and get yourself a 4 foot bush hog or rotary cutter as they are called. If you are mechanically inclined there are many older used tractors as all can help on this issue.