After I got married, my real estate deductions were limited dramatically (because my AGI included my husband's income).  

(warning links to PDF) The West Oakland specific plan puts West Oakland on track for smart, and profitable, infill development that will further boost your appreciation oriented investment angle. 

Would the boost to eventual resale justify added cost?

Perhaps that is a bit dramatic, though I feel as such during this stage in our timeline.

It's simple to use and its plugins enhance it dramatically.

If the place has a bad reputation, 342 units is a lot of tenants to cycle through and replace, and you will need to do something pretty dramatic to get stronger tenants into the community while the majority of old tenants remain.Thus, rather than think about gentrification, you should assume that the area will stay the same, and focus on getting the property for a price where the current cash flow provides the return you desire.  

.: Thank you, that encourages me (gives me an extra boost).

I am coming back again with an incremental boost up on my offer.

After about two years of inactivity and REI study, I developed a strategy almost identical to @Andrew Cordle in that the biggest hurdle to rental properties is capital.I want to actually Invest, and build my asset column, not simply boost my income statement in the short term with a pure fix-flip approach.

In other words the best answer I can give is...... it depends.Deal structure varies from investor to investor , so what you will do on this deal may vary dramatically the way you handle the next.I wholesale & rehab a lot of properties and my typical process is the following:Once I get a contract with the seller I will send it over to my attorney to begin the process of pulling title because I have multiple exit strategies with every investment I put under contract.I always try to wholesale my properties first, if that doesn’t work then I will fund them, close and begin the rehab.When I turn around to sell the property as a wholesale deal, I take it a step further to ensure that I do not lose my deposit.Instead of just taking a refundable deposit for an assignment, I structure the deal with an extra document.