As far as appraisals, you may need to incentive the tenant to let the appraiser in.

Many among the biggest stock losses were real estate, builders etc. 

I’ve contacted him several times but weeks have passed and it’s clear he’s not going to be able to get that signature I need.At this point I don’t see what incentive either the seller or realtor have to take any action at all on my behalf.

My biggest expense is monthly rent and I'm looking to househack so the rental income can cover that expense and I can save towards more properties. 

Certain brokerages will offer incentives to refund various fees after your first few transactions, so be sure to shop around. 

The biggest red flag I see off the bat is your plan to "buying sight unseen."

The Way People Do Business: one of the biggest implications we might face is the change in how others do business.

My biggest concern is that the property only has doors separating the two sides and so I don't really want to live in that close proximity to tenants and I don't want/have any money to invest upfront in renovations (like closing off the doors into something more permanent). 

I would think that HAVAC is probably the biggest issue.

I'm really nervous since this is by far the biggest project I've ever even thought about doing!