I see from your profile that you are married so your wife would need to be on board with a year or two of less comfort via househacking in order to help build long term wealth.

They should be able to tell you how much of the potential rental income with count towards the income requirement and your CPA can guide you on how much you can comfortably afford in a housing payment. 

Also, it sleeps four but I don’t see anywhere I could hang out comfortable with three other people (again- a great way to use the deck).

I have been able to have private lenders in second position, but it takes a great relationship for them to be comfortable or use another property as security.

All in at 70% but what is that max margin(in terms of the %) an investor has to have in order to feel comfortable?

How comfortable are you that the HOA fees will remain $150/ mo? 

Also if you have ANY money to contribute that would help make a partner more comfortable on the initial deals.

Property has gone from being a bad apple to a clean and comfortable place to live.

Being debt free is over comfortable and scared middle class nonsense stuff. 

Normally, we would approach our CPA for this but he is retiring and we would like to seek out a new CPA anyway who is comfortable with doing this transition.