He owns 1031 Federal Exchange and is also a tax attorney. 

I hope it will be a long time from now, but I and 2 other siblings are the beneficiaries of a SDIRA (non-Roth) that primarily owns a 300+ acre timberland tract in Virginia with some cash reserves in the account.

.) - and then for a property, you need down payment + closing costs + reserves.  

Whether or not you subtract reserves for maintenance, vacancy, management, etc. from the annual rent or use the gross amount is a personal decision and I've seen people do it both ways.

On one hand I like that it will probably cash flow (we expected to break even at best) and know there's issues with canceling reservations.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

Assuming interest reserve and contingency funds are capitalized within the loan $250K would be the total equity required to do this deal.

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Higher insurance, capex, reserves, etc.  

, and cap ex reserve fund.