I have been doing extensive research over the past months in the way of listening to a Podcast almost every day, as well as reading realestate investing books, going through these forums and lots of Googling.

I understand the trials and tribulations of working with friends and family, but I am willing to take these on for my first deal.My experience in real estate isn't super extensive but I am a data engineer for my day job with a background in statistics and finance.

I strongly suggest that you visit the market and the team as part of your extensive due diligence. 

If you require a lease extension, give him a deadline to sign it or move out.He told you he will be out this weekend.

Counter with principal only, 1 year optional extension.

If you are going to have a time crunch see if you can negotiate an extension with the Private lender (with penalties probably). 

Nothing was put in writing nor was there a contract extension or any contingencies.

We've found a candidate we're likely going to rent to, we've done the background/credit check and my wife's communicated extensively with the person via text message.

For example, on a 5 year hold, at minimum, I would do a 3 year loan with two 1 year extensions.

Did you buy wel and/or do an extensive amount of rehab?