You've made a lot of general statements about Roofstock without specifics. 

Are you leaning toward a specific metro?

If you have specific questions about property management, I'll be happy to help!

An accountant is a general job title that may potentially do one of many different tasks(bookkeeping, reviewing financials, assurance, taxation, etc)Bookkeepers are specific that they will likely only do the bookkeeping.

Nore the rent control bullet is CA specific and I do not know how ADUs affect rent control in other jurisdictions. 

LLC's main benefit is from a legal perspective.

Alternative is the sherif evicts him and I pay tax and insurance.I know we can have a gentleman's agreement on these things, but im still afraid he might be able to legally sue me if we have a legitimate residential lease?

To do this legally, I know plans need to be drawn and submitted to the Planning Board.

Are you leaning toward a specific strategy like buy-and-holds, flips, or house hacking?

Any HML will want answers to those questions plus a rehab budget before getting you a term sheet for a fix n flip loan for this property.I close these types of loans all the time, if you have any specific questions about the process don't hesitate to reach out.