The challenge is that your capital gain significantly exceeds the $250,000.00 (or $500,000.00) tax-free exclusion permitted under the 121 exclusion, and if you sell your property the amount of capital gain that exceeds the 121 exclusion limitation would be painfully taxable.

I spent 4 years in college in Ithaca (perhaps you did as well!).

Look at this article: http://www.businessinsider.com/college-dropout-bui...This man dropped out of college after his sophomore year (I'm starting my junior year) and began investing.  

Happy New Year, I been on bigger pockets for a short time and have been in research phase as many others here. looking into buy & hold , wholesaling, and college rentals (mostly upstate towns).

There are also quite a few of those old homes that need rehabbed around the college campus.  

But then I wonder why I need to pull permits and hire a licensed and insured ____ to do the work.

More than likely real estate investors are part of their business.Look for the agents and brokers who teach real estate investing at your local community college or local real estate school.Good luck!

I bought my first duplex when I was a Sophomore in college.  

Technically, I started real estate investing about 11 years ago in my last year of college.

We actually had this conversation when we were in Destin this last weekend and he was looking at doing a development deal with one of his college buddies.