I’ve done this method once before, but this time I’m a bit torn on the best approach.

I have more of a legal background approach.

I'm no expert by any means, I've just spent time trying to understand the approach. 

We are approaching 100 guests, if we haven't surpassed it already, and only 1 of them was an issue that required AirBnB to get involved. 

However, given its design and commercial-like feel—originally built as a retreat center with a strong Japanese influence—I’m uncertain about the best market to target for a sale.I’m hoping that someone in this group might have connections or advice on how to approach selling a property like this.

Work with your Solo 401(k) provider and they should be able to assist you with properly approaching your banker so as to get results.Alternately, you can choose to work with a bank that already has trained staff on this topic such as Solera or Titan.

I gave too much trust on their conservative approach and how these "great deals" penciled initially on paper. 

His approach changed a bit upon hearing my decision.

Your plan to rely on landlord insurance and umbrella insurance for protection is a good approach while you’re learning.

Depending on your answers to these questions, you might have a different approach.