If a commercial property is earning a good ROI, the owner can sit on the property forever.

I doubt Community College will teach you anything you will ever use to make money in this business.If it did, the teachers would all be driving Rolls Royce's and living in multi-million dollar mansions--they are not.If you want to learn about SFH's (the bones and the guts of them) vs being a hammer swinger putting up framing (which you don't need to go to college to do)...study to be a home inspector at someplace like the InterNachi... https://www.nachi.org/become-home-inspector.htmOnce you earn the badges you will know your stuff about SFH inspections.But still that's a big commitment and it's not needed to make money in this business...you can hire Home Inspectors, just like you can hire tax pros, bookkeeping, and etc...If you want to learn how to "put in cabinets", "replace a toilet", "shingle a roof", add a dormer, etc...you can learn on YouTube fast and easy.If you want to learn how to frame, get a job 9 to 5 with a framing contractor, and get ready to WORK HARD.Here is a 582 page picture book of how to build a house: https://www.amazon.com/Complete-Visual-Guide-Building-House/dp/1600850227Sit down next to a Keurig Machine with a book like this and your favorite mug and learn at your own pace.  

Honestly, I don't see the benefit of earning what could be Cap Gain money, but put it in a deferred account to someday pay earned income rates on it. 

I'm a career handyman who's just passed his RE license exam and super excited to dive into the world of real estate investing!

I am also looking to move to another career, as I am currently in a commission-only sales job and have not made the amount of money I had anticipated, due to supply chain and payroll delays (needing to wait 4-6 months to get paid on my sales).

I am super fast with numbers, corrected him and the most I can earn is $1.8 million.

Earning cash to purchase rental propertiesHow did you find this deal and how did you negotiate it?

If staying alive is more important than earning a few bucks, I recommend you sell the investment property and purchase a single-family home or a duplex with totally separate spaces so you can control your environment.

Early in my career, I had someone offer to rent for two years and they negotiated a $200 rent reduction each month.

In my opinion trust is earned, and $500 for one service call adds up quickly.