As it was my first deal was I emotionally attached to the outcome, but I eventually found a deal that hit my financial goals and didn't have the same degree of distress.

Their emotion-based issues could be greatly to your profit here, they certainly have been greatly to mine in the past.Good luck to you, Savannah!

Your wasting emotional energy chasing windmills.

Projected figures:Income: $201,300Raise rates as follows: 11 2-bedroom units @ $1,000 each, 6 1-bedroom units @ $725 each, 1 studio @ $625 each, 12 garage stalls @ $50 each, ~$200/mth laundry incomeVacancy (5%): $8,201Gross Income (after vacancy): $155,815Taxes: $26,000 (increase due to updated sale records with county)Insurance: $7,000 (used this placeholder in "existing" even though it's based on projected value)Maintenance/Repairs (3.65%): $6,000Utilities: $2,400 ($2,400 - will move all tenants to ratio utility billing, which will be acceptable based on market, cover common electric only)Property Management: $22,269 (1/3 first month's rent for each unit + 8.75% management fee)Total Expenses: $64,055Net Income: $127,180Debt Service: $86,981 (after refinance into commercial loan of $1,125,000 - 15 year maturity, 5 year lock, 25 year am, 6% interest)Total Cash Flow after Value-Add: $40,199DSCR: 1.46ARV based on market cap (7.5%): $1,695,000 (value add of $286,000)This type of building does not come up often in my market, so I'd love to make it work; however, I also want to be certain I'm not emotionally invested or overly optimistic.

He pays over a month late and I made the mistake of reducing his rent by $500 a while back but it was only supposed to be temporary so that he could save for a down payment to buy the house.

Access to price history on MLS should be sufficient for 99% of the time in these cases.And if it's a property that's super-unique, I'm not sure the history would help that much in determining value since, e.g. with ranches, the price is often determined by the emotions of the (in the case of ranches often wealthy) buyer.

Yes, I am concerned because one item is the removal of any temporary structure… A.k.a.; a child’s playset and a basketball hoop.  

And remember it would just be temporary.

This is not a big deal, you will have many tenant issues and just remove the emotion from it. 

I this was me I would be looking at touristy areas, places where there would be a great demand for temporary rentals.