1) These bonuses are relatively new and I don't think he benefited from the age 30 and 40 ones (and its kinda rude to ask directly if he got it). As for happiness, I think he is happy with his job, especially given his lack of qualifications. Salary is decent, nothing fancy and probably not even 5 digits (based on peers I have at ME4). But well able to support family (3 kids grad from local U) with AWS + prudent spending.

He is fine with regimental duties (parades / NDP / guard duty -> NS boys should understand), and various Air Forces squadrons have random days off during low-key periods.

2) For a period, I think so. in the past, Air Force bled people to the private sector (airports / selatar etc). Then, they started bumping up pay to match and I think the thought of leaving went away. Especially because his English proficiency is bad (he prefers hokkien / Chinese), he prob won't be able to survive in private sector. Military sergeant majors, esp the old school ones, generally are his peers so its much easier for work comms.

Anyways I'm bothering to write these because I know the job market is bad, so hope this helps anyone who is considering Air Force career! also cuz my relative wants me to help low-key promote airforce haha