@Nathan PattersonOur experience with rooming houses has taught us things run best when you have a Den Mother resident in the property - this person enforces the rules, deals with tenant drama; ensures all roomers are respectful of one another and that they do their part to keep the common areas clean.This Den Mother/Superintendent must be someone you trust and can rely upon:  in the OPs example, he was the Den Mother.

I came from a company building 50-60 homes a year (as their Project Manager), and we did that with myself, one superintendent, a bookkeeper and a field guy.

Once I purchased larger apartment buildings, I had live-in superintendents who took care of the day to day stuff.

Again, I was the grunt who got loaned out to any sub like a slave to do the work non of them wanted to do when my superintendent "owed them a favor".

A person is not a contractor under this provision if the person contracts with a registered general contractor and does not superintend the work or undertakes only the installation of carpeting or other floor covering, or painting, or both.The new modified law goes into effect July 24th.  

In a past life, I was a construction superintendent for an apartment builder.

All it takes is to land one superintendent, manager or foreman and the word gets out to the rest of the company. 

My Mom was the School Superintendent in Rockport in the early 90s.

I am interested to learn more and found this below attached the link, it might help you, if not please ignore it.https://www.zippia.com/construction-management-major/Based on the analysis from the link i feel any of the option might fit you.Architectural Internship-->Project Manager--> Property Manager--> Real estate Manager.General Foreman--> Superintendent--> Construction Manager--> Vice president of construction.

My wife and I live in the Denver area I am a construction superintendent working on getting my GC license and she is a property manager for east west urban management (I.e. the glass house downtown) We moved to Denver about 4 years ago from Avon.We have owned our current home for almost three years, we refied in November to pay off our car and debts.We have great credit(over 760)We plan on house hacking with his house and rent it and buy a fixer upper for our next house.We are looking to get into investing however the Denver market is crazy saturated and VERY expensive to get started.