Newbie - need advice on my strategy

[Casey Marquette]

I have sold 5 houses in the last 8 years. I am losing money every time I sell. I frankly can’t sit still and based on my past behavior have come up with a proposed strategy. 

I just sold my condo and will be purchasing a 700K to 1MM primary residence in the Carolinas or Florida. I travel frequently for work and have a strong multi-year relationship with my girlfriend who lives in Michigan. My plan is to rent the property when I am traveling for work or when staying at her house (which could be months at a time if needed).  

After getting some experience I would then buy another property as a primary residence and rent the Carolina or Florida property.  I would repeat this until I had a number of homes in highly desirable areas. I would then have an option to live in many different desirable homes. 

Am I crazy?  What should I be concerned about? What area would be best in the Carolinas or Florida for this type of strategy? 

Any advice and suggestions are much appreciated. My current buy and sell strategy isn’t working.