Craigslist's "Red Paperclip" Story...applied to real estate?

[Dan Schwartz]

For those of you who are unfamiliar, a man was able to trade his up from a red paperclip to buy an entire house in just under a year...

You can read the story and see the various trades he made here: http://en.wikipedia.org/wiki/One_red_paperclip

These trades happened all over North America, and were done as somehwat of an experiment. However, it has always had me thinking about how this can be applied to basic investment strategy, and with real estate in particular.

I'm just getting my feet wet into actually buying/fixing/and holding properties for my own portfolio after doing 60+ wholesale deals these last 2 years, but through 1031 or like-kind exchanges and such...can't this same strategy be applied directly to real estate? ie. trade up from a 1 br apartment to a 250 unit apartment building, through realistically attainable deals, rehabs, financing, and value plays?

Do you see any issues that would arise with this? Or is this generally the idea in the first place and it took me "the red paperclip" to fully grasp wealth building...?

-Dan