I know the house next door to me is a rental, as are two or three other houses within a hundred feet of me, but only one of them is listed as non-homestead on the Hennepin County GIS map.Do I have to convert this house to non-homestead when I start renting it, or can I leave it as is? 

If it is a large raise and the tenants are good you can do it stepwise but if they are going to leave they will still leave so you are prolonging the inevitable.

One is on his 3rd year and says that he'll never leave and the other is on his 9th year.

She paid all of the $2400 deposit herself and felt the need to leave so bad that she has left with the knowledge that she may lose the full $2400.

They leave when they choose regardless of a lease.

Now that it’s getting close to the time for me to leave, I’m rethinking my strategy.

You should never leave your client alone in the seller's home with the home inspector.

If I had a tenant I didn't want to stay, I'd have to either evict them or hope they wanted to leave on their own or pay them up to $4500 to leave (that is another topic altogether). 

@Karen Lipa I would have someone remove that section out of the yard and leave it as is.

Mother-in-law= $1000/M for long term lease, or if AirBnb'ing, $1,600/M.Both of these numbers are being very conservative by listing below market in an effort to get more traffic.Our original plan was to live in mother-in-law suite and rent out main living area leaving us with a monthly mortgage of roughly $700/M.