@Jake GoehringIn my opinion, if you don't already have a source you can go to, (such as an attorney well versed in private lending and a CA mortgage broker who is licensed) to ask about legal, regulatory and compliance issues regarding residential lending in California, you shouldn't be contemplating doing it.

My wife and i had a similar monthly "savings" and we contemplated paying down the mortgage, or investing in rentals.  

So I'd make the case that passive investing needs to be devoid of contemplation or deliberation of how said investment is faring or whether or not it's being tended to.

(I have a wife and 2 kids) I have contemplated paying out of pocket for insurance but it's crazy expensive any suggestions?

Party decides to buy new home and is contemplating selling or renting existing home.

Contemplating switching CPA's.September- After saving for 2 years and losing it multiple times above buy a new to me car. 30 miles in wreck it.

I have contemplated changing markets as well, but I enjoy the hands-on too much for now. 

I've contemplated this question many times (believe I've made a few posts about it).  

I have been contemplating something similar to you, only we're thinking of doing a Reverse 1031 (where you buy the replacement properties before selling the relinquished property - still all has to be done within 180 days, but then you're not rushed to buy something after your rental sells). 

Im contemplating opening up HELOCs for the rest for more access to capital... but worried if its smart move.