At some point, the juice isn't worth the squeeze for us and we just want to enjoy life. 

And if your investor friend’s private loan helps fill in any gaps, it might be worth considering that short-term pain for long-term stability.What do you think you’d focus on first... paying off that line of credit as fast as possible or jumpstarting the renovation to boost cash flow right away? 

It's worth mentioning the STR regulations are relatively new, and I think some properties currently operating are basically grand-fathered with the old permit, and I don't know if being a new owner one'd be able to get a new permit if it's not in the designated location.

As sponsor you have a VERIFIABLE track record of success in same or at least similar investments 2.

When you are getting into raising big dollars from sophisticated investors they are going to want to see a track record and a well thought out and detailed business plan.

I can buy landlord insurance without coverage on roof (wind/named storm peril) but is it worth the premium?

While there are definitely benefits to running a fund, it's tough to achieve success with funds as a beginner because oftentimes investors are attracted to the track record of the person or team running the fund. 

That guesthouse has been here since the 50’ as it’s on record, but has no permits or CofO  If I permit it as an ADU, I can no longer short term rent it.

. $10k in debt does not seem like it is worth filing bankruptcy as you also will have the filing fees to file bk and if you use an attorney it could be another $5k, To me if you can save $10,000 a year then start saving and pay off that debt, as filing bk will hurt your credit wehere paying off these debts will improve your credit.

The lender has a duty to track their loans and recorded documents are notice of the change in ownership.The most serious problem is when a "kitchen table transaction" is used and not-recording the deed is used to intentionally hide the transfer.