The other key to me taking out the loan is that I have enough reserve cash that if I lost my job I could pay the money back right away. 

Hi there,I own a handful of longterm rental properties in Chicago and have sat on an HOA Board for many years.

.#3:  Short cuts are not efficient. 

The key is to identify personal property from real property.

A prudent investor doesn't seek quick riches through shortcuts.

I think I've done my bookkeeping almost every way you can - from not at all -> keeping receipts in a shoebox and handing over the entire shoebox to my CPA -> running 10-key tapes on all the receipts for each category and handing those tapes to my CPA -> DIY Quickbooks -> paying a bookkeeper to manage everything in Quickbooks -> to now doing it myself using Baselane.

One of the key benefits for memberships is that it's a lifetime membership (no ongoing fees or expiration date).

I know it may be against my best interest but I cant bring myself to give her cash for keys.

A prudent investor doesn't seek quick riches through shortcuts.

And due diligence is key with good tips from @Mike G.