He has so much knowledge and seems to know something about literally every subject on this site!

You'd have to add if you have a mortgage if you do.Keep your savings as an emergency fund, and if/when you rent the 2nd place - add that to it and pay it off faster.Using this pay down method, you would pay off ALL of your debts (including the ENTIRE 45k loan that can be forgiven in 9 years) in 2 years.Don't need to sell the cars, don't need a second job, literally just don't blow your money and concentrate on debt payoff.

We're not finalizing the deal until Feb/March 2019 but I'd like to get a jump on this since it is literally my first rodeo with a lease option.  

There are literally thousands of these scenarios of why extra costs occur, those are just some that I came across in the past couple of years.

Like LITERALLY INTO his house. 

Utilities are use-based, for the most part, so keeping them off will, literally, save you less than $100 a month

There are different situations and different models for income/outgo, and different markets for cost/rents where an analysis that is as general, and can best be described as using "fudge factors"...then making decisions based on that "fudged analysis", should probably be flushed out from the start. 

It's a literal definition.

Denver is literally lousy with REI Meetup groups. 

I am trying to learn all I can I am literally spending hours upon hours of research each day for the past few months trying to educate my self on the legal aspect etc.