This enables you to scale in a way that driving can't. 

In my mind "helping them out" further infantilizes and insulate them from the realities of their financial situation; allowing them not to learn from a mistake, but kick the can down the road and enabling them to potential make this same error again.

so resizing it to a much smaller size enabled the upload.

Whichever route I take, I know that I'm planning to build a system to enable the business to be truly passive.

If renting, my rule of thumb has always been improvements/updates must  enable me to receive more rent and/or rent it faster and/or get a better quality tenant. 

I have paid my CPA up to 6 points on a deal, because it was well worth it for me and it enabled him to get the 12% yield he was looking for.

Alternatively, I'm wondering if I should start developing my own spreadsheet to enable the specific analysis I want to perform.

Renting enables "freedom."

In inexpensive rentals, it may be worth it to reinforce and/or level the floor to enable putting down Allure without it looking bumpy, since it will conform to the floor.Another advantage that you didn't mention is that you can replace just a few planks, and not the whole floor, when it gets damaged.

My goal is to purchase buy and hold properties that will increase my monthly income to enable me to spend more time with my family.