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. 

[Joe Villeneuve]

Originally posted by @Dave Foster:

@Casey Marquette, What you're really aiming toward os an asset collection rather than a rental portfolio.  If your goal is to end up with a lot of choices of where to live in nice houses you own there may be more efficient ways to get there.  

Unless you're wanting to get a high end multi family property (think estate with a carriage house or luxury building where you reside in the penthouse) or start a vacation rental or air bnb business, you're going to find that infrequent stay's there will be more hindrance than anything.

Properties that make good primary residences do not always make good efficient rentals.  And you're going to have a tough time trying to rent some live some in there.  It might be better to simply conserve and grow capital for a while.  And use your capability to purchase assets solely for income production.  This doesn't prohibit . you from a vacation rental model.  But it does let you enjoy the best of your flexible living situation while maximizing the return from your capital.

The next step is enjoying the different locales and then later pulling the trigger to buy a primary residence where you love best rather than choosing from primary residences you already own.  

 This hits the nail on your head.  After reading your description of what you call a strategy, I'm wondering how big your trophy case is?  It appears as though you are worried about spending a lot of money each month on trophies you aren't going to use look at 75% of the time.

What you're doing isn't a REI strategy...it's a personal fulfilment strategy (really expensive home collection). I would describe it as a hobby...and a really expensive one. What you're doing here is trying to rationalize your expensive hobby by asking us to approve it. Your not a REI...your a home collector. All you're doing is substituting expensive homes for stamps, cars, art, etc...

Hey, if you can afford it, why do you feel the need for approval.  It's your money to spend any way you want.