Intro & Question - How to switch primary residence into a rental?

[John Oliver Mendoza]

Hello BP community! 

My name is John Oliver Mendoza and I'm a 24 year old software engineer in San Diego looking to get into REI. My family has lived in section-8 housing for the past 12 years and last year I was able to buy my first home to finally get us out of there. I used an FHA with 3.5% down and I've been able to get the rest of my family to cover 85% of the monthly mortgage payment. I actually don't live in the house (no space for me) and I am currently renting somewhere else with my girlfriend, but now I'm trying get a 2-4 unit multifamily to live in and house hack.

My goal is to convert the house I bought last year into a rental and have my family be my "tenants". Doing this will allow me to add that rental income and qualify me for a new mortgage on a multifamily home. I'd really like to get another FHA for this other home, but I don't know if I can qualify for any of the second FHA loan exceptions (bigger family, relocation etc). I will probably look into 5% conventional loans instead if it's possible or more creative financing.

So here are my questions:

Does anyone have any experience converting their primary home into a rental? What is the process? What are the pitfalls? Do I need to set up any business entities yet?

Does anyone have any experience renting out to family members?

Does anyone have any experience qualifying for a second mortgage after renting out their primary home?

Does anyone have any experience finding duplex/triplex/quadplex in the San Diego area?

Bonus:

I'm new here so I would love to network with everyone and know more about the various real estate groups around the San Diego area.

I'm so excited to get into real estate investing and have been listening to the BP podcasts and reading a variety of RE books. Let me know if you have any book recommendations for starting out. =)

Thanks!