I’m really early into the research phase but would be prepared to “pull the trigger” over the winter (eg purchasing a property to setup the tents) but ran into a bit of a “wall”.I’m pretty close to Blue Ridge and love the area so have considered a STR there for a while.  

I think it's a great way to enjoy the benefits of your investments without triggering a big tax bill.

Hey Paul, congrats on pulling the trigger on your first property.I'm also in CA (on the central coast) and invest out-of-state (Detroit).

If you have a mortgage on the property and transfer it to an LLC (the LLC would be a different owner) it could trigger a due-on-sale clause.

I signed up for a mastermind class that teaches you how to invest in STRs and pulled the trigger on a 2BD/1BA house in Pittsburgh, PA to operate as an STR.

So please please please consult one before pulling the trigger.

Very helpful and all responses have triggered additional questions for my tax guy.

@Jordan Dzubak we played with the idea of getting something at the Lake a few years ago, but ultimately never pulled the trigger in large part because so many neighborhoods were modifying their C&Rs to prohibit short-term. 

I really appreciate any input or suggestions before I pull the trigger on these large expenses.

If you don't, then you essentially have no insurance on the property.But, it's when the lender is notified of the new insurance coverage that will actually notify the lender and then they will trigger the due on sale clause.