Luckily my attorney and I still filed up "holdover tenant" which keeps our position in this forever growing backlog. 

I’m now 8weeks behind schedule with rehab because the village building inspector takes forever.  

If you are an OK landlord and have everything under control with long term good rental market, I would hold forever and pass it down. 

There may a distance/code reason for the well-on-other-lot configuration (in which case you might end up with a defacto double-lot property for forever. though possibly with 2 homes---sort of duplex-ish).

@Ramon Ramos That has been the standard for Fannie Mae for years, if not forever.  

I hope I would respond the same way he did & I will forever have respect that he didn't put a price on his own integrity.

@Tchaka OwenI put the management fees in there with the assumption that I won’t be managing forever (after I am no longer house hacking).

He was a professional, is a friend and saved my project (and life) while teaching me how to build along with many other life lessons I will forever be indebted for. 

Downside is she's MUCH stronger and opinionated than me so my stress level is higher sometimes because she is forever wanting me to change this, yell at this tenant, evict that one, etc.

In contrast, if this was your forever home and being an owner-occupant was the plan in perpetuity, there are still clearly better or worse deals you could make.