Private lenders won't necessarily need an appraisal, but they will expect you to make a convincing argument for that valuation, based on recent comparable sales.I see I was unclear before about what I meant by the property "supporting" the debt.

It is fluid depending on the situation.  

Regarding the term  "1099" I meant to say "W9".

Well what i meant by the finance guy was that he helps you out either by finding a hard money lender which he says he knows a lot of, and also other solutiions for funding which in my case i didnt have the capital but had the credit.

The cap expenses are meant to be a reserve fund for future capital expenses.  

In my market, that would have meant having around $100,000 to put into the property.

That is not what I meant by insurance.

These statements are meant for the original questionnaire, Nicholas.

Can anyone who has replaced vinyl siding recently elaborate on what he might have meant ?

I spoke to a realtor yesterday about this same thing and according to him there are a few issues 1. if you do owner finance, you must own the property out right or have no debt on the property2. i'm not sure if i understood 100% what he meant but he said in order to do lease to option, the bank is going to analyze the market rent, but the kick is that the market rent must be on top of the original note.