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?

It's one of the most important elements of making a deal happen.

This could allow you to build equity steadily, reduce the immediate demands on your time, and potentially refinance in a few years to access funds for future investments.Alternative Approach: Small Multi-Family Property: If you're open to it, a small multi-family property (like a duplex or triplex) can combine elements of both strategies.

This can be cap ex to the building's common elements or cosmetic like a new lobby that you as a landlord may not view as a worthwhile investment but the owner occupants may.

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?

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?

I used a combination of leveraging my business line of credit, HELOC and partnerships for my first couple deals before adding in private lenders.