If not, there is a failure-to-file penalty for failing to file or extend your tax return by the original due date of your return, which in this case is April 18, 2016.  

Periodically he has seen that others have written about the same problem - but how were they overcome?

I think I fell victim to the former on my last offer because it was a HUD property going for an asking price of $300k and the realtor told me it went for $360k (It was owner occupant bid period so presumably investors couldn't bid, and it went for a price that doesn't justify a rental- someone probably fell in love with it and wanted to live in it and pay 60k over the asking price although Idk why bc the property needed around 35k in repairs).

There were a few years of pain, but then over a period of 3-4 months, I started getting certified letters in the mail requesting I refinance those houses under the HARP program.

The wholesaler will usually know a network of investors that buy properties in that area and will advertise the homes to them that they have under contract in the hopes that they can generate a profit above the contract amount within the contract period.

Another tip is to shop with many lenders for a longer amortization period if you need cash flow.

That's what my thinking was: either have a creative solution that one of the tenants would be willing to accept, or anticipate as OO.Chris Mason, I was under the impression that refinancing out of an FHA loan requires a longer 'seasoning' period that 6 months?

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.