Our lot size is 7300 sq ft and main house is 1700+ sq ft.Location: San Jose, CA- We were thinking to potentially design the ADU such that we could have a wall (or a door) that allows us to separate the ADU into a 1 bed/1bath for self use (or rental) and another part which could be rented separately on AirBnB as needed.

I am putting together a pitch book for an $8M ground up self storage development.

A real estate business is not different then any other self employment income.

Add maintenance/cap ex, vacancy, PM, misc and this is likely negative more than $500/month even if self managed (much more than the negative $200 that you indicate you are ok with) 2) if you are behind on mortgage, how are you going to handle being negative $200/month, or more like negative $500/month?

With regard to your "DST" and as with many highly structured tax vehicles that have a potential "self dealing" quality to them, there are a number of potential potholes you can easily step in along the way (e.g., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).

No personal experience with PMs since we’re local and self manage, but there are 1-2 that I’ve heard good things about. 

Mine is boredom between Self Storage and Country subdivisions.  

Given that the industrial market is softer than the prior few years, I intend to buyout/wait until current leases expire and leverage the space into self-storage. 

I self-manage and produce $700 in pure cash flow each month.Lessons learned?

.: Quote from @Chris Seveney: @Dana YobstBlows my mind how he is out there still teaching classes and going on as nothing happened but it sounds like these debts are not getting substantially paid down.As many of us know, one of the main reasons he's able to continue on is with the help of this other self proclaimed criminal https://weclosenotes.com/ep-nc-03-protecting-yourself-using-a-corporate-veil-with-aaron-young-from-laughlin-associates/ Using a remote entity to limit liability is a life blood of insuring investment into all types of job creating, life saving and life improving business development.