I admire you.

Only in very special circumstances can you have two (2) FHA loans at one time and for the most part, house hacking does not meet the requirements...you will need to be prepared to use conventional financing (or some other form of financing) for your 2nd, 3rd, 4th, etc. purchases.I admire that you are thinking the way you are...If I could go back, the HH strategy is exactly how I would have started...I believe that rental housing, and in particular multifamily investing, are the best routes toward financial freedom...so much so that I have been educating my 19 year olds in every way possible so that they are prepared to execute a HH strategy when they are done with school (maybe even earlier)...I believe you have the right mindset and are the correct path...Best of Luck!   

Telling people what I do and how I do it went a long way in gaining admiration, trust, and interest in others investing in ME.

In my opinion, those who are trying to invest w/o money are doing an admirable job trying to get ahead. 

They are about to miss out but it's admirable that you were willing. 

Hey Alex,Find an investor that you admire or who is doing what you want to be doing, then ask him/her what kind of help they need. 

Robert, You are demonstrating admirable character and chose to do the right thing rather than the number driven business decision. 

Again, I really admire the hustle that all of you have. 

Not sure how you can help her get qualified for Section 8, but just follow the directions on the Section 8 site to see what to do.As far as your idea overall, although it is admirable, it is more dangerous for both parties than you think.First, it sounds like you would like to set up a Lease/Option agreement with her...which would be very hard to do with a Section 8 tenant. 

The fact he's being upfront is at least admirable!