Challenges?

Reason we are trying this strategy is just due to the fact that just like the rest of the country there is limited supply in this market.

The IRS will require them to charge a “reasonable interest rate” if they supply seller financing.

Expensive markets can be a challenge, but here are deals to be had, depending on the amount of work you are willing to do.

The plus side is the airbnb supply has fallen and we have noticed a HUGE increase in our gross STR rents, roughly 20% higher then a year ago.

Sometimes I question whether there is some real estate investor challenge I am unaware of where investors actively try to one up one another with new ways to toss their money down the drain. 

The biggest challenge, more than handling maintenance, is managing tenant relationships and understanding the legal responsibilities.

This is particularly important as you acquire more properties.Transferring the Property: If you're thinking about transferring your current rental property into an LLC, be aware of potential challenges that I have personally seenMortgage Implications: Check your mortgage agreement for any clauses related to property transfer.

Compared to other parts of the country, in my opinion it's definitely more challenging to find good deals here based on everything you mentioned. 

It just goes to show that challenging yourself and pushing the boundaries pays off big time.