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

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.

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

Lease options are the vehicle of choice here, until I sort out how to get to the other side of the ceiling imposed by debt to income ratio.

No house is perfect.

So depending on what you want buying a business might be the better choice for you. 

There's some great choices, but what it comes down to is what your buying strategy/criteria is. 

I am not looking for the perfect deal, I just want something that will improve my financial position better than just dumping all my money in a high yield savings account or something.I don't need to live in the nicest place.

The basics of a seller financed deal are that the title co or closing attorney (if there is one) or seller’s attorney draws up the warranty deed transfers title, the promissory note evidencing the debt related to the transaction, and either the deed of trust or mortgage (whichever is being used) perfecting the lien against the subject property.  

With a thriving tourism scene and steady year-round visitors, it’s perfect for short-term and long-term rentals as long as you are choosing an unsaturated asset class.