Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

The country has massive debts and deficits. 

Some buyers enter these agreements without fully understanding the financial commitment, often influenced by overly optimistic advice.

One thing I will say, and do with it what you will, if you are digging out of a bad financial position I'd suggest RE is not for you now. 

I wish I could say that I'm venturing into real estate investing for some benevolent purpose like providing low-income housing for the needy... but financial gain is certainly my angle lol.

I am continuing to make payments on the existing mortgage from the payments received from my buyer, which I am assuming is a characteristic of a wrap-around mortgage where the seller acts as the financier for the difference between the existing mortgage and the sale price.

On the other hand, if you're aiming for long-term rental properties, getting prequalified with a lender specializing in traditional loans or DSCR (Debt Service Coverage Ratio) loans is key.

I sank every dollar my rentals provided back in to paying off debt and acquiring more properties.

Property must Debt Service 1.006.

I am expecting to do 3-4 deals per year until I get to 20 properties or so and then snowball the debt so they are all paid off by retirement.