My question is do I need to have a deal closed before I approach a lender to help refinance a property or can I talk to them about my plans (no deal yet) and see if they would be willing to help me refinance properties in the future? 

This approach can work if you have a property manager managing your multi family house hack, I have had clients take this approach and they give up 8-10% of their monthly rent in turn for not being bothered w/ tenant phone calls. 

This is ultimately not the most cost efficient approach but my point is it can be pretty easy to start familiarizing yourself with the basics.I’ve only been an investor for a couple years but work as an estimator in the construction industry, which has been a valuable carryover to my REI career.

Chances are that I will allow him to move in, but I'm not sure of the best approach. 

Give 30 days notice to vacate.Another approach is having them sign a month to month lease at the current rent amount.

I never done an out of state renovation before and not sure what approach is best to take in this scenario; One of the unit is renovated and is ready to be rented out however the other unit need quite a bit of work in order to get it ready to be rented out.  

I love this approach and use it myself even though I have my own rentals as well.

Also, since we are approaching snow season has anyone tried finding tenants during these times?

Does anybody have any experience with this kind of problem or idea how to approach it?

I would approach it with a happy and friendly attitude and bring it up to him directly.