I've been using it for over 4 years for self showings with no issues.

If you are going to self manage your property, then I would not want my tenant to know my name.

If FNMA, FNMA allows transfer of deed to LLC if mortgage originated after June 1, 2016 and original borrower owns a majority interest in the LLC and any 12 months of owner-occupancy is first met:https://servicing-guide.fanniemae.com/THE-SERVICING-GUIDE/Part-D-Providing-Solutions-to-a-Borrower/Subpart-D1-Assisting-the-Borrower-with-Property-Related/Chapter-D1-4-Transfers-of-Ownership/Section-D1-4-1-Information-Relating-to-Transfers-of-Owner/D1-4-1-02-Allowable-Exemptions-Due-to-the-Type-of-Transfer/1041300841/D1-4-1-02-Allowable-Exemptions-Due-to-the-Type-of-Transfer-09-09-2020.htm

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

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.

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.).

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?

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

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.