Also make sure to consider all the aspects you can including the tax differences. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Many people get this confused thinking that is take-home (NET) income, when it should be BEFORE taxes GROSS income. 2.

It’s a tax office, so I suspect they might be waiting to see how their business performs and the impact of technology before deciding.Thanks in advance for any advice or insights you can offer!

Sounds like you have a pretty poor security system.Even with a good security system, having a tenant provide ID is the first step in a professional screening process. 

I found this one https://www.titlesearchcourse.com/faq/ its 69$ and the person who created it also has a youtube and specializes in tax foreclosure properties which is what i do.

The only part that Property 1 pays on that loan is the escrow for property tax & insurance for Property 1.Thank you for your insight.You need to look at purchase price to determine cost basis, not how you financed the purchase.

I could also see 15% corp tax and the whole no tax on tips thing.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

If you need financial help, ask under the "Finance, Tax, and Legal" forum.