My gut says you probably want/need separate policies for the different entities at the very least - the purpose of having them is to keep things separate in case of a lawsuit, so combining insurance would pierce the veil and allow someone to come after everything. 

Some info: - Combined lots would form about 5000 sq feet. - Currently zoning allows for 2 unitsThank you all in advance! 

Do you mind sharing what your combined value is on your 2 properties?

However, there’s one aspect of the website that’s raising a bit of concern for me.I live in Santa Barbara, CA, and from my experience, the median home price here is generally at least $1.5 million, and in most cases, I rarely see anything priced under $1 million.

I am not the one making the payments, but it's still on my credit report.My limited income, combined with being a co-signer on the loan, results in a less-than-ideal DTI ratio.Under these circumstances, what type of loan or lender should I focus on?

This is one of the problems with housing in lower tier markets because on the surface they appear to be great value but capex makes it impossible in many cases to keep them up and running and therefore the cash flow from your spread sheet rarely translates to reality.

Refi: The piggyback HELOC is a good tool for quick access to capital, but since it's been delayed and you're already tired, it might be worth waiting for a combined refi and HELOC.

I have some ideas about how to make this possible (partnership, private loans, refi/heloc, or combination)...But what would you do in my situation, if you were starting your portfolio from the beginning in 2024?

And having done this for a long time, it is the rare renter that cares about the land.

Due to the nature of the STR property criteria in Cape Coral, it's very rare that a STR could be converted to a successful LTR.