If you have not contributed post-tax dollars into a traditional IRA, the total amount converted is taxed at your normal income tax rate and the Pro-Rata rule does not apply, but in this case you mentioned you have an IRA so I'm sure it does. 

The hardest property for most folks is normally the first property since it is hard to figure out what a "good deal" is.

It's a fairly simple form and I think it should help answer a lot of questions.We should scrutinize any seller finance deal, there absolutely is more risk than a "normal" sale. 

It is normal to have second thoughts, but if the numbers work; I'd go through with it.  

However, we were basically gambling on every transaction at this point in our career.

We dont have a hot tub at home, so if 2 properties are the same, we would rent the one with a hot tub to enjoy something we dont normally have. 

For the last 10 years, interest rates were artificially low-it was not normal. 

I did pay myself a salary last year and plan to do so again, but I won't be able to produce the standard, "...last two pay slips" type of documentation that normal conventional lenders want. 

Electrical wiring has been redone to normal.

Section 8 tenants will generally not tell you issues in the property and then tell everything to the inspector which gives you a short period of time to get a lot of work done or you will get abated and lose the rent for that portion.Section 8 tenants are MUCH harder to evict than normal tenants.Happy to talk more about this if you want.