How secure you are with your current/future income, as a piano instructor,  and your ability to cover all your costs should the rental be vacant for an extended length of time, or if there is an unforeseen expense. 

I'm considering a rental agreement that states the move-out date in the contract (with option to extend under certain terms), and has them pay the full 2-3 months' rent up front, with a half-month security deposit also due prior to taking residence.

You can purchase the home at the sheriff's sale auction by out-bidding (the bank).After the sheriff's sale, the tenant still has six months (maybe this was changed recently to 1-year)  period.  

We extended it straight out into the swale at the lower slope. 

Can it be extended? 

We have down payment money, but not for multiple houses in a one year time period.

Would like to fix it up and pull equity out of it within a 2 year period to buy a duplex.

Identified as a non-conforming structure, the town added "CAN ONLY BE REPAIRED/MAINTAINED UP TO 15% OF CURRENT ASSESSED VALUE IN ANY CONSECUTIVE 12 MONTH PERIOD."

From crowdfundinsider.com:"The most important restriction is that companies can only raise $1,000,000 in a rolling 12-month period using these new regulations."

:Alternatively you could take an additional 18' strip out of the back yard and make overflow parking along the end of the current lot, just past the garage.Do you need a permission from a zoning board to extend parking lot if it's free amenity and inside your property lines?