Study the market.

I've spent the last year following the real estate market and learning more about it, finally feel ready to make the jump to invest (especially since the deals are coming out to light). 

When the market is more balanced, then it may make sense to buy a primary and convert it to a rental when you move.There are exceptions, but you will need to learn how to really analyze a property to know when the numbers make sense.

@Jake Berlinoff market

If the property appraises at $500K, 25% higher than purchase price, either because you bought it for less or due to market appreciation, then you essentially get all your $100K back.  

BiggerPockets can be a great resource, and I know there's tons of information available on the Fort Myers market specifically.

Hey everyone,I'm beginning my direct mail marketing campaign through a third party company as of now.

If you do a case study also consider what market appreciation and mortgage paydown would occur in both scenarios.

How much it rents for is not determined by what you'd need to make it a good investment, it is determined by the market. 

Currently, the market is still short on supply so when putting in offers you need to put on the 'seller' hat and think what they would want.