If you have an Iphone, you can create a separate folder for your photos which you can save your business receipts.An alternative option is using an online storage platform such as google drive, dropbox, etcBest of luck

Therefore, I have a hard time committing to a house hack which contributes greatly to my problem of raising capital for a conventional mortgage with a 20%+ down payment instead of alternatives such as an FHA. 

Things have to go really bad from here, as I see it, for the office to underperform alternatives in the next few years, from a cash flow perspective. 

Alternatively if you feel confident in the higher value, I would ask if the lender is open to doing an independent appraisal ordered by an AMC instead of a desktop one. 

I would not invest in real estate with a retirement account.Its too much of a headache and likely not that much better as an investment alternative within a retirement account1) Real Estate provides tax benefits for individuals who own them.

As an alternative, would a cash-out refinance, a home equity loan, or a HELOC make sense for you?

Alternative options include offering a significant down payment, a lease-option agreement, a joint venture, or a deferred closing to align with John's timeline.

Because your alternative is zero income.

. ;-)  While I wait for delayed communication from them, I am looking for alternate management in the Canton area. 

I'm not sure how fast you want to scale, but I see that as a feasible alternative if you don't want to go through the process of either BRRRing or the fix and flip.