You can run different scenarios all day, but the only way to make it work is to either buy the house for less money or extend the note over a longer period of time.Or, you can sell the house on a wrap, which you proposed as your plan.

I have the ability to come down when needed and for extended periods.

Like you as a mortgage underwriter, I have many years of experience being a professional supporting real estate investors as a CPA, but I now wanted to become a real estate investor myself.In late November of last year, like you're doing this November, I wrestled with the question of investing locally with a 4-unit purchased with FHA financing vs. investing out-of-state and got a lot of great advice.Like you, my goal is to retire within the next 10-15 years via real estate investing.As a result of some of the advice I've read through the forums (I would recommend you pay attention to guys who have been in real estate for decades like @Jay Hinrichs rather than the younger folks who are often just pushing their turnkey products) and speaking to investors at local real estate groups, I decided that given my place in life I would be wiser to place my bets on California appreciation over the next 20-30 years rather than investing in some beat-down property in Cleveland for an extra $400 or whatever in cash flow per month.Given the facts that (1) I could get into a property for a measly 3.5% down, which would free up cash to invest in other places if I so chose, (2) I was already throwing away rent every month such that I could still be cash flow negative of $650/month (what I was paying in rent) and still be better off because a portion of my monthly payment would be building my equity and the rest would be tax deductible, and (3) I'm in my 20s and have the time to take a long-term view of appreciation potential, it was a no-brainer to go the FHA 4-plex route in LA, despite the fact that it is one of the most expensive markets in the country.This isn't to say that the process was easy.  

Bad neighborhoods will cause a long time period to rent out to better class of people.

If you don't have the coverage or have a small amount once that is used up the insurance company is off the hook and you are responsible for the rest.

The only post-sale right of redemption periods that I know apply are the HOA and tax liens. 

Our next purchase will be a quad plex that we will live in one unit and rent the rest.

I recommend like the rest mentioned to search turnkey on here and make sure you interview them very closely.  

@Dawn Brenengen on C class and lower I don't think anyone I know has EVER given a deposit back period...

Is there a set period wait/time , of which you have to wait before you can claim Rental income as " Actual " income , via your taxes ?