Now I am totally confused!  

It is very embarrassing to admit that a woman who has been an entrepreneur, taught college, and accomplished a few things in life, could be so totally taken in.

I totally understand that it depends but I think what I am looking for is a bit more input and guidance.

The current owner listed last years income as $51,000, but currently has rents at (for the five separate units): $650, $750, $800, $825, $1125 (the math doesn't totally add up so maybe he changed a rent payment at some point). 

I usually hold 15% total for these.

I resided in the home until summer 2020 (total 2 yrs 9 months) and then deployed overseas for the next 4 years; selling the home in June 2024.  

Yup, most renewal fee's are total BS fluff.

He believes that area where he will be buying the new homes is going to appreciate and attract more MTRenters, but now, the big difference is that he would now have 3 properties that can go up (or potentially down) in value, go up (or down) in rent, and three times as many vacancies to fill.My back of the napkin assessment is that for only a drop in $200 a month in cash flow, he would control a lot more assets with growth potential and as rents rise over the coming years, the combined rents will increase to a total more than the single rent.HOWEVER.

Quote from @Conte Cuttino: Property is in C+ area but in a different School district that’s B-If I sale I’ll get 30k profit after 9 months.If I keep as a Long term rental I’ll have to convert the garage into a illegal 1 bed cottage at an additional cost of $35k leaving a total of $107k left in this deal after 70% refi and closing cost.

It's called a payoff statementif it's a big lender you will not buy the loan as it will take forever, you are better just paying it off. you then can foreclose based on the total balance owed to you which is both loans and any accrued interest. regarding fixing property or selling as is, that really depends and needs to be evaluated on a case by case basis