Condotels are more difficult to get financed and typically come with higher interest rates. 

You can list your MTR on Furnished Finder or Zillow as a 30 day+ stay, and see if the monthly rate drives demand in your market.

I work for an automotive shop and get paid flat rate so my pay fluctuates.

The ARV for the property or the rental rates once done if you plan to keep the property.

I'm wondering how people go about leasing their section 8 properties when max rent allowance for a zip code is significantly higher than market-rate (non-subsidized).

I wanted to become adept at sourcing off market deals for other investors so I could get deep discounts for them and also for myself How did you find this deal and how did you negotiate it?

If I go to rent it out at some point that's a negative cash flow of nearly $1400 assuming rents and rates stay the same.

You buy a problem to get a discount.

Pre-Housing Crises (pre-2008) interest rates for investment properties were 6.5%-7%.

I refinanced to a mid 2% rate a few years ago and did not want to do a cash out refi.