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).

Here are the  IRS regulations that will answer your questions whether to capitalize or expense certain expenditure. 

Sell off enough units to recoup expenditure?

See the problem I'm having is knowing the right percentages to place within the expected expenditures. 

And 8% for capital expenditures.

I specialize in condominiums in my area and at this point I've looked over so many disclosures and financials, I can tell pretty quickly based on the number of units and cost of cap expenditures about how likely they are to have an assessment in the near future and for what (roof, elevators, etc.) even if it's not on the agenda.

During these 3 years because I'll be paying a premium interest I'll only be cash flowing around $100 a month after accounting for repairs, vacancy, capital expenditures, etc.

This method will provide us with cash up front, higher rent, and an opportunity to sell the property sooner without additional expenditures on such things as advertising.V.

The response that I got back from him was that he intended to reject the amendment since there are other interested parties on the property.From experience with buying investment properties when something substantial comes up for capital expenditure items like roofs being at the end of their useful life, is the request that I made a reasonable one?