I started investing once I turned 18(I lost most of it (whoops)), but I started focusing on safer investments and learning about real estate over the last two years.

Most people suggest finding an independent agent who can shop multiple carriers as the best option and that is a good idea also but know that some Indy agent's don't want investor business so I'll say it simply Indy's are great but not all Indy's want your business. 

Personally I like the A-B neighborhoods, south of the mason dixon line (the winters aren't as harsh), because it's a safer more consistent investment with the rental clientele you're working with and it's almost guarantee'd you'll get every dollar invested back, of course if you buy the right deal.

Also, do you think it’s a little safer to sub to into a brrr? 

Both are very well versed with investment properties and can shop multiple carriers for you. 

Should I keep shopping around?

@Alex Hujdus I've started the conversation with an agent and we plan to shop around for a lender.

I'm back in the market shopping around Sacramento.

Or is it okay to work for a private one/two man shop- where Im friends with the principal and who has all the knowledge and experience from working for the big firms...

You can then start shopping for another, and rinse/repeat.