I do see your point on the security deposit.

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.

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.

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

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?

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

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

I ask everyone I meet who they recommend, like I asked my realtor for bankers and contractors etc, and in turn ask the bankers for realtors they like.

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