Part of the problem is I am in a situation where I can increase my J.O.B. income about an extra $80k a year for a few years or more if I want but it will require travel and high stress so I won't be able to focus on wholesaling.

I have a trusted friend who is overseeing the rehabs that gives me confidence to invest out of state.  

I am an agent as well and have access to mls  and am confident about the comps, so I don't expect to have any trouble finding a buyer for them they are solid deals . 

@Brad Woodhall - I am very sure of the comps in the area, my mother lives about 3 minutes from the property and I actually grew up in that area, so I am pretty confident.

Fannie Mae "Second Home" financing, 90% LTV, for the place where you frequently travel for work.

I'm originally from the Caribbean, but I'm now an american nomad who likes to learn about the world through international travel and by living in different cities in America.

Maybe I need to educate myself better to gain more confidence, but it seems to be the least forgiving on a misstep especially in an expensive and competitive market like San Diego...

His biggest complaint was the amount of time it takes to get paid.Since you will do lots of traveling, you should keep your eye open for abandoned properties  (driving for dollars while doing your day job) and perhaps you can locate a deal.

I realize part of finding a deal is making it happen in the moment but I want to educate myself as best I can before I get into an offer and right now I don't feel confident in this strategy.

I recently signed up on BP, within few days I gathered tons of info on REI so far it's a wonderful learning experience with BP/Prodcast/Books I'm very excited to start my REI Journey with the help of BP, it's giving me day to day motivation/belief/confidence to pursue my dreams.