@Tchaka Owen I house hack the home that I currently own which will remain that way.

Make sure after conservative projections you're satisfied with the potential income - it should be significantly more than a LTR.  

This is kind of a two part question, so I'll start with the current home I own. 1/3rd of my house was left to me and in 2017 I decided to purchase the remaining 2/3rd's and move in.

Good contractors are always busy , material prices remain the same in the winter , employees still get paid the same hourly wage , the days are shorter , and the working conditions are worse .

You can deed the property to an LLC after the close, but the note will remain in your personal names.

None of those behaviors fit my definition of sweet or cooperative.Here's what I would do if I were in your shoes: if you haven't already served written notice, it's too late for January and you'll have to be satisfied with terminating their lease at the end of February.  

We do have a copy of the lease and there is options to renew, but ofcourse these remain tenant options.

Where's the remaining $85k coming from?

I remain sadly convinced that the reason most people don't want to do any handyman work as part of real estate investing is because they think they're above this work, not because they think they can't do it well or there's a sharply compelling reason for them to focus their efforts elsewhere.It's also the party line of every real estate guru out there that you should never do your own work.

You likely can't move your current 401K while you remain to be employed by that employer.