Rohme Williams I would like to talk with you more about the current market you live in to gain more insight on the area.

Pay someone elses home off or buy my own home and gain all the tax benefits and equity and JOY of use. 

I have prior experience in stock market investing but I have started to gain interest in real-estate investing as well.

Not to mention all the headache dealing with the tenants, repairs, etc.If I sell the property, I will make (after cap gain tax @15%) around $550k.

Heck, a boat load of actual property managers aren't worth their weight in dirt.Remember: cheaper doesn't mean you'll make more money.You can start by going to www.narpm.org to search their directory of managers.

Will we pay capital gains on the amount we cash out? 

Commercial C-1 zoning may allow mixed use or retail on the frontage but this is a hard stop to gaining conventional financing. 

So far I’ve read 4 books published by Bigger Pockets or their members and am gaining a lot of insight into which direction I wanna go when I finally do take that leap into investing.

Some of the best experience that you'll gain is on the job training. 

I want to be able to get right into real estate investing and gain experience so I am ready to buy/sell homes as well as be the best real estate agent I can be.