Re: Keep my Grasshopper or .... ?
Sounds like you want something, other than a mower to help with around the house work?
For what you mentioned, snow, blading, tiller, mowing, etc type work, I'd be going to a JD, New Holland, Kubota, Mahinda or other local tractor dealer and see what they have in a "scut" or "cut" tractor. At least determine a size that you think would work for the size of not only your yard, but doing extras if needed when the time comes.
With just a mower and then getting what few attachments that would work with it, you could get a much better "used" machine that uses 3-point or front-end attachments.
Then just get a small push mower for all the finer trim work around trees, rock walls and things you can't use a larger tractor around.
I use a push mower, along with using my large front deck or my mid-mount mower around my farm for doing pond bank, small orchard areas, fence line, all time when I mow my yard, my mom's yard, and rural roadside for about 5 acres total. No one can or should have only one mower to do everything when doing acreage. Besides, you will come to a point where one mower is down for repairs, so you really do need backup mower.
1967 Cub Cadet 102-Kohler K241(10hp) Kept as original as possible.
1990 Kut Kwick CL20-60-Onan P220(20hp) Front deck/rear steer industrial/commercial mower
2003 Craftsman GT5000-B&S engine(24hp) Manual transaxle