My son was hired by the same company he interned with in college, but he still could not get a mortgage until he had 2 years of full employment with the company.  

People that sell information understand that it is easier to make money SELLING the dream then finding a grand slam deal over and over again.So they sell systems and generate revenue.

However, the buy & hold area is so much different than flipping that telling you I have a deal that will cash flow at 1% is about the same as telling you I have a pair of shoes that will fit you without knowing your shoe size.Flipping employs a fairly simple and defined formula that everyone can use.  

To facilitate my ability to make said purchases, I transferred 401(k)'s from prior employers (administered by Fidelity) to a new custodian (IRA Services Trust Co) into a rollover IRA.  

Therefore I was thinking to operate 1 of the 3 rental units as a vacation home (inspired by last week's amazing podcast) aiming to keep the unit occupied enough to generate a similar or even higher income to the other two long-term units.Does anyone here have, or have had a similar set-up, and would like to share their experiences with me?

According to the Bureau of Labor Statistics, only 1 in 9 adult Americans was self employed in 2009: http://www.bls.gov/opub/mlr/2010/09/art2full.pdf. 

If that is how it works in your state, then listings are an easy way to start generating income.

I am currently employed in the Gaming Industry in Biloxi.  

Can I hire the General Contractor that I am employed with to serve as the the GC of my renovation and still oversee the project myself?  

I have more local knowledge about Toledo than I care to admit. but aside from being born and raised there, most of the employment I had early in life had me out and about, and Ive lived in just about every area and still have relatives and close friends that live in every area.