I reeeally want to get back to the point where I'm maxing out my investment vehicles I have with my advisor but also really want to continue contributing to improving this duplex because it's old and still needs a fair amount of work.

I did a loan once for FHA using a bill of sale that the buyer had, he sold his ATV and showed signed/dated Sales contract along with the cancelled check and VIN # for the vehicle he sold and thats fine.

Now I am working on my application, and there is a requirement to enter the NYS Department of Motor Vehicles Issued Driver's License Number or NYS Department of Motor Vehicles Issued Non-Driver's Photo ID Card Number.

Sadly, you must not have any experience with DSTs as an investment vehicle. 

We can't really see the rest of your situation......and don't know your immediate goals...... but with a decent amount in the bank.....why not just purchase an adequate vehicle with cash?

I sold a vehicle and paid off a credit card (2500 dollars)  to improve my savings and borrowing rate, now they’re asking for the following:1.

Currently we have a small sedan and figure we would need to invest in a new vehicle to get around. 

It is a great retirement vehicle plus it's fun for the family. 

I know the insurance industry is highly governed and regulated, but these warranty companies (home and vehicle) like to fly under the radar.I think this will be the last time I ever have a home warranty unless it's an accommodation from a purchase like this one originally was.

My goal is to retire using rentals as vehicle to do so.