I look up for school, crime, and amenities, focusing on the convenience in the perspective of the renter.

It's convenient to work with the same reliable title company no matter where your deal is.

My wife and I bought our first investment property and on the fence about rent or flip, although we are leaning toward flip.

Again, being new you might not know what is an acceptable finding, this is why it's really important you find an experienced partner or at least someone to lean on (unless you already have that) on your first deal or two.Good luck with this deal and I hope it works out for you.  

Im leaning toward a contract sale and hard money rehab since it seems to be a little more flexible.

Potential Options:Single FamilyHouse-hack4-PlexI think I am leaning towards the 4-plex, as it allows me to go as big as possible, while still feeling under control.

On your other question, I like leaning on Rentometer.com if i have no other resources.

We are leaning towards a home with separate guest quarters.

Doing just multifamily from the get go is not an option.Do you recommend any portfolio loan lender or strategy which would be able to provide convenient terms for acquiring properties through the fund/LLCs?

Specifically, I'd love to learn what areas in Southern California would be worth investing in and how to identify and fund good deals (currently leaning towards single and small multi-family rentals).