For a little background - I have been taking a big loss on this property for the last year for reasons out of the control of my property managers.What would you do in this situation?

One thing that hasn't been brought up is if you put a property in an LLC, it MAY be subject to California Rent Control, even if it is a single family home.

Our owners find the statements easy to read, and the platform allows for setting alerts at the property level, creating custom and reportable fields, and offers robust reporting features.While we appreciate RentVine, one feature we miss from Appfolio is its very granular access control.

I don't observe too many people buying multi-family in the Bay Area with our rent control laws but there are deals here. 

If you start a JV in name but do not give your partners proper control and decision-making rights and the deal goes bad you open yourself up to serious consequences which can lead to SEC violations with extremely high fines.Lastly, you can offer the project up to investors who have no voting or control.  

Also make sure you are comfortable with some holding costs if the units don't get rented right away (if vacant).Also look into if there is rent control in the area that the property is located.

The biggest difference to me is that YOU have control of every aspect of an active investment, while somebody else is in “control” of a passive investment.  

Mostly NYC real estate companies uses Yardi Voyager and not the Yardi Breeze that most people here in BP uses.Even if you get a job that uses Yardi, you will have limited access on what you can and cannot do just because the role you are in unless you are a Controller/CFO.

However, I don't know from a practical point of view if it's doable 2) Condo vs townhouse vs cashflow: I noticed condos  and townhouses are way cheaper in fort myers FL ( however risk of hurricanes) and maybe more opportunity for cash flow.

Your strategy takes advantage of your employment cash flow and ability to control discretionary spending.