Hello Nicholas, there are a few drawbacks: -Complexity and Scrutiny: This approach could attract scrutiny from the IRS, as it's not a typical way to manage rental properties.

Yes - you should be able to find a lender that is "AirBnBRRRR" friendly - most DSCR Lenders will require the full 12 months of STR history but a few that specialize in STR can qualify less than one year, typically with AirDNA projections or some common-sense mixed underwriting approach

I know that some hosts require their guest to refill the propane tank, but I actually do not like that approach.

As I continue to save and approach an acceptable down payment threshold, I am debating a few things and looking for some advice/insight. 1.

I think if you approach the conversation with tact, you might be able to feel them out. 

Idle capital is generally not good, but when you are getting into a new investment approach, stagger your investment.  

Short term rentals can be lucrative but come with higher variability and management needs.My Take:It might be beneficial to consider a mixed approach—drop the rent slightly under market value to secure a tenant and stabilize your cash flow, while simultaneously exploring the short term rental market.

Before being approached to help with the development costs, I had considered on buying after the development was complete; 4 lots then having 4 homes built, selling 2 and keeping the other two to rent out.

Experience is one factor that some investors may require as a condition, but overall, you can get a DSCR loan with healthy credit and reserves. 

So often I see people with all this money and success, but their health is deteriorating.