I don't really know, this is my first attempt at this, and given the unique property, really can't afford to spoil the opportunity. 

While I am licensed to practice law in Ohio and also do a good bit of taxation work, every situation has its own unique set of facts.

First, you and hundreds of other agent are prospecting these people in this situation so you wont be unique to most of these potential sellers.    

I seek out a property with "issues", whether property condition, management, or a combination of the 2.  

So its a combination of increasing costs and relatively flat rents that puts too much of a squeeze on cap rates.Still a lovely place to visit or to live....but maybe not to invest in my opinion

Unit 1 currently rents for $850, after improvements (adding central air to whole property, W/D in basement) we will rent for $950Unit 2: Total gut job and we will rent for $1,150Income/ExpensesTotal Monthly Income: $2,100Expenses: $830.57, Saving: $315, Total = $1145.37P&I: $531.45 + $40.26 (additional $7,500) = $571.71Insurance: $100 per monthProperty Taxes (yearly): $23875% vacancy, 5% repairs, 5% CapEx (we are replacing roof, gutter, new A/C, and 2nd unit will be brand new everything) = $315 per monthMonthly Cashflow: Before Saving: $1269.63, After Saving: $954.63For our calculations, we use the before saving value because we both have full-time jobs and will be dumping a large portion of our paychecks plus cashflows from this property and other properties into an account so we will have ample fund if something were to come up)ROI:Purchase Price = $82,000$33k (down payment) + $2.5k (extra cash needed) = $35,500Total Monthly Income = $2100Monthly Expense = $830.37Monthly Cashflow = $1269.63ROI = 12 * $1269.63 / $35,500 = 42.92%ROI (w/ savings) = 12 * $954.63 / $35,500 = 32.27%Cap Rate = 26.36%Cap Rate (w/ saving) = 21.75%Additional Factors:As stated above, this is one of the last parts of Oakley that is being improved upon and the average home value is $199,500The house next door (that is the exact same as this property) sold last summer for $165,000With the combination of the two above, one of our exit strategies is converting the property into a single family down the roadThank you for reading!

My firm has a number of property management clients who write their unique properties and firms liability and workers comp with us while writing some of their more standard properties with other agents. 

But interior stairs that require trim work and a combination of oak and pine we outsource.

Bought a 4 unit and a house (two different parcels combined at one point) in Historic Kenwood in 2012 for $139,000.

With that said, @Rochelle Wilkinson your son is in a unique situation; you and your husband both own your own companies, so it looks like the entrepreneurial spirit is strong in your family.