That-being-said, gated communities do offer additional privacy that may be of importance to you.

The seven houses totaled approximately 3 million dollars in fraudulent loans.Five Indicted For $4.1 Million Mortgage Fraud Involving Homes ...https://www.justice.gov/usao-ndoh/pr/five-indicted-41-million-mortgage-fraud-involving-homes-medina-and-gates-millsA federal indictment was filed charging five people with taking part in a $4.1 million mortgage fraud scheme involving six luxury properties in Medina, Ohio, and one property in Gates Mills, Ohio, said Steven M.

General Dynamics, Ratheon, Avnet (Fortune 200) Bills Gates bought a huge swath of land outside of Phoenix to build a high tech city.

Bought under market, saw future in the HOA plans to gate the community as well as several upgrades.

I know you can lead one to the gate, but the one led has to open said gate. 

Personally I don't know if I would go with a commission based career our of the gate, but that might force him to acquire the needed sales skills.

Quote from @Heather Gates: Hello Everyone!

I want to make a smart decision out the gate.

I think that working for someone else would be a good idea because you would likely have more free time to work on real estate and you are much more likely to have a better paycheck right out of the gate.

The pricing tools won't be perfect out of the gate, you have to spend a little time learning them and what prices you get booked at and which you don't but it gives a great baseline.