Challenges?

My challenge is that I don't know when exactly I will be able to obtain the STR permit from the city, so I don't want to convert guests too prematurely. 

Managing vacation rentals remotely sounds like a unique challenge..

The challenge for me will be to attempt to mirror this type of financing approach to Southern Calif. real estate. 

. #922-2, pp. 86–95) (noting that upwards of 90% of transactions on the Subject MLS offer buyer agent commissions of exactly 3% during the class period, with the exception of the MARIS MLS consistently offering 2.7%)....Although it is true that a nominal commission of $1 would satisfy Section 2-G-1 and Defendants agree such nominal commission is mandated, Plaintiffs have produced evidence that no transaction within the Subject MLS took place using a nominal commission.

Challenges?

Real Estate is rewarding, and challenging.

What are the biggest challenges people have faced with this.

Will they defend my report in an IRS audit?

That process has direct lender involvement.Where the challenge lies, is when unsophisticated "investors" with no experience, no money and no reserves use creative financing (often called wrap, subto, lease option, seller financing, land contract) to purchase properties and along the way there is a "hiccup".