I am looking to invest in apartments and rolling my 'dead equity' in something larger (apartments).

If you’re planning to scale you can look into larger ERPs like Buildium or Yardi.  

My 8 unit has come with a larger learning curve because it was horribly mismanaged and a total value add.

(larger principal paydown each month).Please don't PM me.   

This means that you don't need to create new accounts, like rent, and expense categories that are specific to rentals and real estate, but Buildium is expensive and for people with larger portfolios. 

If possible find the larger companies, my current and former company both have more than 1000 employees and have been operating for decades in this market.

The only difficulty is I’m trying to find a multifamily property in an older housing stock area but nonetheless an owners unit inside a larger house is the goal but hopefully I can get lucky with the items you pointed out as well. 

Timelines and capital required are obviously higher when pouring larger foundations for a tower and craning modulars together on the site, but if you had a blue print/drawings in hand their timelines are as follows:6 weeks in the factory 1 week deliver Laydown site Shuttle to actual location where crane is Crain in 4-5 days3 months of finishingHope this is helpful!

In IL we are allowed to discriminate in certain ways on small owner occupied buildings, it is a completely different set of laws to larger buildings.

Meaning, if you committed to live in a property for 12 months, and you have done so...then you can buy a smaller/larger home at any time.