You're in San Francisco and I'm a local in the area that Conner mentioned.

As others mentioned, expect some deferred maintenance too.

For those who have rental properties, can you mention what costs you generally cover for your tenants? 

Lease/option requires a lease (that does not mention an option), and an option (that does not mention any lease).

NEITHER retail buyer nor the wholesaler have the actual CASH to buy the home, as mentioned before.

You don't mention the market, but even in a good cash-flowing market $500/unit not not easy to find especially when fully leveraged at today's rates and also trying to borrow down payments.

The Professor mentioned that it was 'supposed' to move one foot per year to relieve pressure.

Maybe, maybe notYou have to weight the pros / cons along with the risks.Your BP mentions you are 'new to real estate'.You are getting into a new asset class along with a business(I consider a STR more of a business than an investment).How much will you save in taxes?

My sales guy, Ben, mentioned that he did 20+ deals since joining the program and 8 of his deals were funded though the Springboard Funding program. 

If the new property has less of either asset class (1245 or 1250) then the difference is subject to tax at the rates mentioned above.