I must admit that back then I felt a bit uneasy about it until I got some mileage on those relationships. 

Estimating repair costs, calculating ARV and things of that nature, I am still uneasy with.

I did not push through either since this made me uneasy.

I know that the rents for that side of town tend to average lower than other areas.These are things to just think about and to double check being that you are feeling uneasy about the deal.

But I think they are now just uneasy about tapping that equity.

The 2 family is still owned solely by me, and not in a LLC which makes me very uneasy.

The buyer was fine with my fee because it was a good deal but the seller had a lot of questions and seemed uneasy I was making so much even though I agreed at the price they wanted (no negotiation).

Yet, here's the thing: although we'd get a new rental property with great loan terms, and we can seemingly afford the new home payment/mortgage, it makes me a bit uneasy to take on that much more debt in a down market, but mainly because the amount of interest we'd be paying is astronomical if we did nothing to pay down the principal early on or over time; every month for years would average $2,700~ of interest payments, so we'd be breaking $100,000+ of total interest paid if we do nothing just a several years into the life of the loan.

But im still uneasy about hiding that from section8, I don't lie, I dont want problems, I want full transparency.Also please advice about First month, last month and deposit.For regular renters this is a requirement for me, But I called 2 section8 landlords and non of them asked for last month, only the deposit, as section 8 pays for the monthly rent.

Some people get really uneasy when they have large amounts of debt.