@Mike Bagden while I would typically not recommend selling a property that could cash flow that much, this sounds like the hassle and capex expenditure you'd have to deal with will negate the benefits.

I am designated the manager of the LLC and as such get to make all the decisions as far as daily operations and expenditures up to a certain amount.

Get a copy of the budget and ask about any upcoming assessments or major capital expenditures before purchasing a condo (new roof, paving, replacing windows/doors, painting the complex, etc.). 

Many investors also add a line for capital expenditures of around 10%.

How about setting funds aside for vacancy, maintenance and capital expenditures?

If the delinquent dues were very minimal then the HOA could raise the monthly fee and start to build up savings for the capital expenditures in the near future (and the utility loan) but how do you get people to pay their dues?

You want to know the price of the property, full rehab costs, and long term capital expenditures before you sign as the buyer. 

Taxes, distance from attractions, internet service, age of property and recent capital expenditures will need to be considered on each deal.

When I say they will cash flow $100/month, that accounts for an expected average of all expenses including: mortgage, taxes, insurance, vacancy, repairs, capital expenditures, etc.

I aim ever so slightly higher in the expenses category, estimating 11% for total property management costs (including leasing fees) and 15% for repairs/cap ex (though one could argue capital expenditures will be about the same regardless of the rent amount).