It took about 2 years and I built a thriving STR business as well as buying and selling houses. 

I grew up in the town I buy my property in.

I am considering partnering with one or two of my associates which would allow us to buy a larger property (likely a nice duplex or triplex) since none of us currently have the capital for this down payment individually.

The lady that bought them down was trying to buy an Island in Clear Lake CA that I had worked on with another developer in the late 70s and it could not be built on at all period.. she had this big dream would never have happened but Remington stole her 10k and she went on the war path..

How are most investors strategizing there (fix and flip or buy and rent)? 

You don't have to have that to get a loan or buy a home, but it will help. 

I used to use spreadsheets, then moved to when QB as my portfolio grew, now on Digb because I have multiple LLC and I don't want to have to buy QB subscription for each.

I have given some very strong consideration to buying in Detroit.

After we live in it for at least a year, we will move out of the 4th unit and buy another multi-family and do the same thing.

However, if I sell my business then do I no longer qualify to buy a property in the future?