What's the best way to save and organize digital receipts and to snapshot paper receipts? 

I called Zinus a few years ago to confirm since model numbers matched the Zinus on Amazon.

The whole East bank is going to be a different universe over the next 10 years.

@Karl Kauper with a SF you can require the tenant to take care of lawn and snow, but they might not be up to your standards. 

If looking to scale flips and create systems around it to minimize your time and involvement, I'd highly recommend putting a team in place that can handle the day to day operations. 

So the loan for the rental shows as a debt but the income is not reported to the bank where we are trying to get the new loan.

You will need to have experience in short term rentals to interest a lender on this.

2) I haven't yet reached out local banks, but seeing the quotes from brokers makes me wondering if Banks may be better? 

I believe there are license allotments in many towns near and around Denver so you want to make sure there is a license available for the basement unit before you factor this into your cashflow plan.

I have nothing bad to say about them since I haven't worked directly with them and they must be doing something right if they are one of the biggest ones in the area.