After collecting tenant pass-throughs for the year, do you pay the property taxes at the end of the year or the beginning of the next year?

. $500,000 was tax free due to being married.  

Medford also just voted to increase property taxes which is another reason to act. 

A FHA 203k Loan is where the purchase price and rehab costs are rolled into a single loan.Assuming you have a respectable FICO you can buy, with a FHA Loan (3-5% down, a 30 year amortization schedule, and a residential loan rate) AND because you closed personally, you will not have Asset Protection, in the form of closing in the name of a LLC/ LLC taxed as an S Corp, or an S Corp.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

As you know its near impossible to find a good cash flowing deal in CA due to sale price, taxes and lack of inventory.Last one I closed on was over off of Germantown Road it was a great 2 unit that needed a little TLC for $160K but passed an inspection and was livable.

You are trying to say you will use the " investors" to fund community programs, that sounds like a charity because there is no earning on the investment.  

You filed two full year tax cycles and the numbers are similar (no greater variant than 1%) they maybe yes.Generally depreciation is added back as income BUT only the 40% portion you own not all of it.

I had constant issues with the local government and the taxes were absurd.

Other advice, especially that pertaining to tax benefits, is also highly appreciated!