Great thread!
Joshua, Your post is making me nostalgic because I loved the simplicity and the economics of living in my 4-plex a few years back. I'm now 2 houses and 2 kids later on my owner-occupied journey, and while the bigger house and bigger equity I am currently in are nice, I loved living free with 450/mo x 3 units covering my $890/mo mortgage + tax/ins back then.
Back to you ...
- I second idea of entity owning and you renting. I did that as well.
- I can't speak for commercial financing, but as a BUYER of your building it wouldn't give me much heart-ache to value your building with you in it. It helps to know current rent roll, but for me it's just like buying an occupied SFH that I intend to rent. I do my own projections and determine my own valuation based on after you move.
So if you are selling, I am not sure it hurts you to stay, especially if you rent at market rate from an entity. Save the hassle and expense of moving.