If you end up having a vacancy with no cash flow, it hurts much more than when you are able to offset with cashflow from your other properties.I would recommend seeing if you are able to diversify a bit with some local or out of state properties that do cashflow some, even after Property Management, that way you could start to support these homes.

Hey John, welcome to Sac BP -- I'm a local broker and property manager, we manage 100+ Airbnb listings and generally recommend investing in Multifamily as opposed to Single-Family.

I love to connect with others here who might be willing to share advice, resources, or success stories if anyone has tips for me as a beginner or any recommendations, I’m all ears.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Some lenders do see a 99-year lease..especially one that’s asumable..as pretty close to ownership, just with an asterisk.

Any recommendations or suggestions on how to navigate this?

When you say professional quote do you recommend just paying a trusted contractor to do a walkthrough or do you first recommend getting an inspection to figure out what’s fully wrong/needs to get fixed before bringing in a contractor?

That is your competition.I believe my recommendation will prove accurate.  

If it's not already grandfathered in as a multi-unit, you take the lot area divided by 750 sqft/du (for R-8 zoning), and that's how you come up with how many units you can do. See

Quote from @Kandice Morgenstern: I recommend you consult an attorney.