Ideally was thinking a duplex, triplex, or quadplex to get started and use an FHA loan but I also have a private lender that can possibly help with up to $200k worth of a down payment.

What paperwork should I keep a paper trail of to make things like taxes and other situations better/easier for myself?

If you don’t have a certain amount of funds set aside for these situations as well as your portion of closing costs and some extra reserves for once you close then you’re likely not financially ready to be buying things.

Be sure your lender is comfortable with this, as many fear giving folks primary loans for properties they view as having a high probability of being turned into a purely investment.

Here's a little background on Tenant situation...has 2 or 3 young kids, an adult sister, an aunt with her male friend and the lessee has a male friend, that all appears to live in the apartment but aren't on the lease.

Hire a loan servicer - plenty of discussion and recommendation on BP on this topic and some recommendations for servicing companies 

If you're worried about cashflow, why would you do a 15 year loan with a higher payment -> meaning negative cashflow?

Hi Joshua,It really depends on your situation and your specific needs/wants.

this is regardless of furnished or not.if you do not get rid of the tenant, the situation will degrade.  

The deal fell through because I couldn't line up the financing during COVID......God/Universe has a way of looking out for us...As investors, a crucial skill we develop is to take our emotions out of the situation/deal, but that is hard when we have invested a lot of time and money into a deal.