I currently work in an Aviation Machine shop and I'm looking to use REI as a vehicle to leave the industry as a whole and maybe eventually move from the W2 Employee to Self Employed in the cash flow quadrant. 

I have a friend who was a full-time employee with the Miami Dade County School Board and she left last year to become an agent full time.

I'm about to dip my toe in to investing but banks don't like me since I'm a tipped employee.

I am looking to hear about how mildly experienced to extremely experienced investors structure their businesses and teams. Do you have assistants, do you consider bringing property management in house, etc etc? Are th...

I currently own a 2 family and live in one unit.. my tenant is a city employee and has job security.

@Christopher Dunson I think the real question is, will your team have employees or not? 

@Dave Foster gave me some great advice previously, and based on my new understandings, I want to restate my objectives here to make sure that I know fully the situation and my options.I bought a new home in 2003 in the San Diego area, and rented out my old home, which I purchased in 1996.

It eventually became impossible so I switched to a digital system and trained my employees to handle them all.

My predictions is that it’ll reach the $700k mark in next 8 to 10 years (our market is crazy) @Dave Foster says sell and I definitely like avoiding taxes but I’m not sure if that still applies in this case. 

@Dave Foster is a knowledgeable Qualified Intermediary which you will need.