I've seen some businesses that have done this in the past where it was an oil change business and it was converted into a coffee shop or restaurant.

This would not be an ideal situation for any tenant and I feel I need to put the idea of house hack aside unless I can find a unique property that has multiple standalone units, one large enough for my Brady Bunch and potentially several other units to offset the note.

A 401k is an employer sponsored plan, so there has to be an employer.

I haven't really exactly figured how much I will need for the business, but I imagine $25,000 would be plenty initially.As a rough estimate, I imagine if I put 20% down + 5% closing costs on a $500k property (what I consider to be an average/nice house in my area), that would still leave me with $165,000 in savings.

Specifically, really steep roads  will interfere with your Winter-season rentals and can even be an issue in the Autumn with the rains and leaves.

Still, I think it could be an opportunity for the right investor and the seller.

I want to go grab coffee with him anyways to talk about REI, so maybe he'll be even more understanding!

Start interviewing GC's at their job sites instead of a coffee shop.

This is by no means intended to be an endorsement of working with or working without agents, wholesalers etc.

Well screened tenants in B class properties will never be an issue no matter what pay method.