I see Detroit as a possibility to keep investing.

Keep investing and moving forward.

I will be keeping in touch with all real estate investors to gain all perspectives. 

Your post is under the house-hacking section, do you plan to house-hack and live in this property that you purchase in Jacksonville.If you are planning to live here in Jacksonville, it is important to choose a good neighborhood that you would enjoy living in.I personally like the 5 points/riverside, San Marco and Southside/Baymeadows area.These areas have more resturants/activities than other parts of Jacksonville in my opinion.

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

$3,000 for a personal return (filing single) and 6 properties (no LLC or Corp) does not seem reasonable.

I don't think you're going to change the person's mind by being aggressive.Yes, money is important...but it's not the only thing. 

In the ideal scenario, we picture keeping the property as a cash flowing asset forever and letting our kids deal with it after we die.BUT, if that doesn't happen, and we decide to sell in 7 years or 10 years, I'm going to kick myself for losing out on the capital gains tax exclusion of $500k.  

I personally think you can, and if the former owner redeems, they get cutover timber land.

I’ll keep running numbers as you suggest and see what comes about.