Anything i should look at to determine if i should continue on with the buying process before calling out an inspector?

The property search feature where you can search for ownership by estimated equity % is pretty neat!  

. $5,500/yr for IRA)- Ability to access up to $50K of your retirement funds tax and penalties free prior retirement via participant loan feature- Greater protection from creditors- No need for a custodian + checkbook control- Exempt from UBIT on leveraged real estate - Tax-free investing with built-in Roth component - and more!

Someone who is sick and had a bad month, could easily continue to have bad months.  

You should also have been and continually shopping local smaller banks and CU's working with their commercial lender on something that works, if you have some cash saved, a decent job/income, and a good credit score, you should be able to get fix and flip loans fairly easily from a small bank.

Personally, I would call a few local property managers, tell them about the area, size and features of the property and get an estimate from them.  

If it continues to make you money, there may be no reason to sell at some point to invest in your current city.

If you cease to occupy the residence as your principal residence for a continuous period of one year or more, the interest on your mortgage loan may not be deductible for Federal Income Tax purposes."

As long as you are "continually employed" without gaps and you can show that it is part of your "career growth" you should be fine, in my experience.

yeah 10-20k discount doesn't sound like much for a flood damaged property.I saw a realtor in Houston  here on BP mention that Houston Association of Realtors (HAR) added a feature to search for Harvey damaged homes , not sure if there is something similar in FL.