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

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.

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

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.

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

The rest, put you on near-worthless drip campaigns, don't understand calculating the offer price based upon rents - property taxes - insurance - MNT & Vacancy percentages, etc.DM @James Wise to schedule a chat with him!

Conversely, if new houses are being built frequently, older properties may struggle to maintain their value.Property taxes also play a significant role.

You might even want to setup a C-Corp (for tax and liability reasons as well) to manage the business with the guests and pay rent to your LLC. 

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?

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.