As a prudent buyer, you should strive to pay a price that makes given the current actual income and expenses.

First option would be to short-sale if that is what is required.  

I would think that San Diego is too expensive of a market to wholesale in

The property currently cash flows around $1,800 a month after operating expenses.

So for arguments sake, let’s say I’m making $200/month in spreadsheet cashflow on a given house after expenses/reserves, and reserving $75 each month for capex expense.

Raleigh does require no more than 2 listings per house.

So then the house is 10% owned by The Person, and 90% owned by The LLC (income and expenses shared accordingly).Now this year say I want to take the same percentage (10%) - and say it's a flat market and the house is still appraised at $500,000.  

He says he doesn't have to pay us capital expenses because we didn't actually pay that, the previous owner did.

If you aren't using it personally because you come to Disney alot and like the resort for your lifestyle, its hard to justify the expenses/assessments. 

It will require homework and legwork though.