The two 4-bedroom units even have two full-size washer and dryers each! 

Alternatively, once you have a full time job (or an employment contract), you should be able to qualify for a loan and utilize a Down Payment Assistance program.

I am no longer employed with the Company. 

Tax-wise, profits are taxed at your ordinary income rate, and frequent flips may subject you to self-employment tax if classified as a dealer by the IRS.

DSCR or Fannie/Freddie loans can go up to 75% on single family homes, multi family homes (2-4 unit) max at 70% if you stick with Fannie/Freddie.Other things to consider would be:Paying points for a lower rate vs higher rate with no pointsIf going DSCR - Prepayment penalty term (0-5 years)The lower the loan size ($200-250k and lower), you should consider paying up to 2 points and doing a 5 year prepayment penalty if going DSCR.

In Chicago you request a CHA Burden sheet and that gross number minus utility allowance will be what you get in addition to making sure bedroom size is adequate.  

Our manager looks at employment, rental history.

For a rule of thumb, replacing a commercial boiler can range anywhere from $20k to $150k, depending on the size, age, and efficiency.

Chiefly, it says "Minimum lot size: 8,500 square feet, or 6,500 square feet for lots of record," along withMinimum lot frontage (width): 80 feet or 60 feet for lots of record.

So, for OU (open use) they have gone back and forth whether they would or would not allow based on lot size or otherwise a STR in that zoning.