Its never a bad time to buy real estate.

There's a very good chance the issue(s) you face have already been discussed and answered.Ask questions in the appropriate forum.

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

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..

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.

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.

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?

Quote from @Emma Campbell:If we have a Lowes business pro account, and in Month 1 we buy $1000 of materials for properties in 3 different LLCs, it sounds like manual effort is needed both to pay off the $1000 balance by making payments from each LLC's bank account for the amount it owes, and then a separate manual effort to record and assign the expense transactions in the bookkeeping software.