Have your main influencer (spouse if applicable) read "Rich dad pot dad" let them know it's just so they can understand where you are coming from.

How about a pre-paid Visa card?

You have your building, you have your own apartment in there, and have the benefit of your potential rental income to list on your mortgage application.

My dream scenario is to rent for 25ish years, reno it, live in it as empty nesters for 2+ years, then sell without cap gains (up to $500k or the then applicable amount).As a side note, I would keep the rental in my wife's name to keep the excellent interest rate.

Be careful what you ask on an application and what you deny tenancy. 

If that works then $20 higher for the next applicant.

I'm also curious what vendor(s) you have selected for DCFC applications. 

The property is actually south of Boston but what you're explaining is probably applicable in this situation although it says that no one is living there at the moment.

Personally, I'm much more inclined to hire a professional bookkeeping firm where all the aforementioned issues are addressed and taken care of vis-a-vis software that most likely might not be able to make it past a couple trivial use cases

I'm looking for direction on how to go about charging application fees.