I had a buddy who invested in Orange because of the cashflow but he ultimately got out due to high vacancy rates and less than desirable appreciation. 

I ultimately land on this like I do all things with parenting - I'm trying but who knows if it'll be effective.

You can survive without a pool only if you are walking distance to the beach and even then you will do much better with a pool.2) Tampa - A more urban market. 

My ultimate goal is to become a real estate investor, except I don't have any prior experience in this industry and am still a bit lost as to where to start.

Its a whole different strategy, which makes it an opportunity as well.Still, there are hundreds of residences built in the 1950s and 1960s south of the tracks, especially in Gulfport and Biloxi, still standing after surviving both of these storms. 

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

They can just as easily change their move out which may ultimately hurt you financially more in the long run if they are delinquent. 

Financially speaking, I'm still saving, but the goal is 50k saved up (all costs: closing, fees, down payment, portion of rehabbing costs) by this summer with my fathers help on the cash all while I continuously save 50-80% of my work checks to fund for rehabbing this property and I work off my second job and "survive off of that."

He is ultimately responsible for the property and oversees the management company.

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.