Starting out - Looking for Newbie Advice! (SD-NYC Areas)

[Dimitri Michaloutsos]

Hi All !

I've recently discovered BiggerPockets/Rookie Real Estate Investing, and as a huge consumer of podcast I'm already hooked! All of their episodes thus far have encouraged posting on their forums so i hope this is the right area (despite being 26, i'm awful with message boards/blogs/forums etc) for this sort of post. 

My name is Dimitri, a NYC native who after 26 years left the city for a working vacation out here in sunny San Diego. I've worked in finance ever since leaving college and have been a personal finance advocate for as long as i can remember. I would consider my current situation, in terms of retirement, micro/macro budgeting, and my career income to be in great shape but i'm really looking for new avenues to take to create a passive income stream. My father has owned property my entire life and has had great success but is very localized to the NYC area and too be honest, i would love to make my own way and learn on my own with passive advice from him. I've picked up numerous books over the years, downloaded tons of hours of podcasts and am a sponge for advice/knowledge of those who have already done it and the path i should be taking.

Right now, i'm just adding to the downpayment fund while learning all i can about the pre-deal stages, and am having trouble determining my niche (living in multi-family and renting out the other units, buying studio-1/2 bedrooms and renting out entirely, etc) in addition to avenues of funding (smaller downpayment w/ insurance, 20% down off the bat). Additionally while i love San Diego i'm afraid it's my destiny to end up back in NYC and die there one day but am nervous i won't be able to afford to actually to buy anything there that would ever realize me any sort of gain and i'm apprehensive to buy where i don't live and manage through a company (so i'm unsure if buying something in SD would make sense if i'm only going to be here 2-3 more years).

I hope my situation is a common one and hope to hear from a plethora of you seasoned vets with any/all advice!

Thank you very much for the read!

Regards,

Dimitri