People are always looking for that perfect beachfront escape.Another reason these areas shine is how friendly they are to short-term rental owners.

Chris you would know if I used AI  ( which i dont know how to do frankly) spelling and punctuation would be perfect and anyone who knows me knows that cant be possible.

We’re not perfect, but we’re willing to improve and make things right as we strive to be better.

In a perfect world an assignment (like @Chris Seveney suggested) would be recorded with each transfer of the note but in reality that does not occur.

If I know anything, it's that I/we are definitely NOT perfect and we can always do better.

That is as close as you can get to perfect alignment between GP and LP. 

I completely agree with the advice and I'm perfectly okay with not charging him rent.My concern is that by treating this property differently from all the other units in the Series LLC, I may be opening myself up to a situation where I'm weakening my LLC protections even if I keep the financials separate and in order.

My own garage fridge was my kitchen fridge 20 years ago and still works perfectly. 

Or any tips for mitigating risks when market timing doesn’t align perfectly?

Starting small with solid fundamentals and not waiting for the "perfect" deal was key to getting started.