Finally, I was a president of my 5 unit townhouse/condo in roger park, and it was very interesting in how we had to raise our HOA fees in order to meet capital expenditures...it seemed like when our toilets crashed or went away to toilet heaven, all of the others did too.  

We are differing on the utilities, maintenance, capital expenditures, and vacancy rate.  

You were missing Principal and Interest from your mortgage and also Management expenses.Based off of that I put your numbers into it.Rental Income             $2375ExpensesManagement               $190 (8%)Insurance                     $125Capital Expenditures   $71.25 (3%)Taxes                           $325Repairs                        $237.50 (10%)Interest                         $412.50 ($110k @ 4.5%/30 yr)Principal                       $144.85 ($110k @ 4.5%/30 yr)Vacancy                       $118.75 (5%)Electricity                     $250Water ad Serwer          $50Total                             $1924.85Cashflow                      $450.15Looks like pretty good cash flow from that.

Needless to say, they were not happy with my revised offer based on the real numbers and the deal fell through.When I did the due diligence, I went and talked to every tenant (there were less than 20) to verify the financials, walked every inch of the property to look for needed capital expenditures and deferred maintenance, talked directly to the utility companies...

The challenge on your side is that you have education related expenditures happening now and on top of that you want to also invest into cash flow producing properties to offset your current liabilities.

Look for something that was built well and will not need capital expenditures for a couple of years.  

Other notes: my strategy has been to front-load my capital expenditures such that my SFH's are "new" when I am done - roofs, HVAC, etc - so that my capex line items stay low down the road.

The reserves that we did have, the former board repeatedly tapped into to cover small expenditures less than $10k which you are not supposed to do, and they did not fund the reserves for future projects (such as painting the community, paving the parking lot, etc.), and we owed over $98k to our reserves when I took over.  

Of course, such "savings" typically come with increased spending over time versus making the expenditure up front.

You make up the cost of rehabs by buying lower, you don't usually get to ask much higher (especially on capital expenditures like a roof)