Having a partner not experienced in real estate will make your decisions more difficult than they need to be.

I took 3 semesters of trade school classes in the subject before realizing the school wasn't going to deliver on their promises.

Even with my lack of experience it seems like this may not have been the most intelligent real estate decision.

I have a crew that I have worked with in the past that can handle everything except the licensed trades.

I say you made the right decision.

Like I said, I own one property so this would be my first ever cash out refinance (I realize that financing like this is not easy to get these days - but I will look into that after I make a decision to go forward or not), so was hoping I could get some more experienced insight.

Craigs list has a "skilled trades services" category (or something similar).

Are you hiring a general contractor that will be overseeing all the other trades, or are you acting as the general?

Paul I would check with a 1031 exchange company.Yes there are people that do these owning the property less than a year.The expectation though is you open yourself up to the IRS trying to challenge you or disallow the 1031 later on.This is why I say it would be best to talk with a 1031 exchange company about your specific situation.Then you can make an informed decision going in.

You might consider a trade; fix up in lieu of down payment.- Does it come with a tenant and what is that tenant paying?