@Rafael Ramos All your goals contradict each other:(1) Cashflow: buy Class C & D properties2) Appreciation: buy Class A & B properties3) Low Crime: buy Class A & B properties4) Why would you want your investments to lose money to lower your taxes?

These are all lower $ properties and not the strategy you use.

My expenses are lower in Stessa and my CapEx is higher.  

The HUD guidelines suggest a certain rent amount, but after inspections, the figure came back significantly lower than expected.Additionally, do you have any general tips for working within the bureaucracy of the Section 8 program?

Looking for any creative input on how something like this could be structured.Taking part of the purchase price of real estate as a charitable donation and using said deduction to lower your taxes is tantamount to sending a cover letter to the IRS with your return requesting an audit.  

If you want the seller to accept a lower offer, you can’t offend them.  

Plus, multifamily properties often qualify for owner-occupied financing options with lower interest rates and down payments.As for timing, here are a few things to consider:Market Conditions: Keep an eye on local market trends.

You can have a lower sales price home built in 2005 that could give you more problems than a more expensive home built in the late 1800's.

If I were to do it over again, I would strive for higher class properties and would not have purchased anything below class B.Higher class properties typically have better tenants, lower turn over costs, less tenant issues, etc.  

Also see if monthly gap might be lower as a mid- or short-term rental.