Not a pilot, but in engineering and fairly recently left SG to return to AU.
Rents in SG went crazy last year (and I know they did here in AU too, but the starting point was much higher already in SG), the two bed unit, 75sqm in East Coast we had was 2.9K and went up to 4K per month and they were still climbing, the LL got 4.4K per month after we left. A bit of advice, search URA rental transactions on google, this provides the actual rent prices as all rental transactions need to be stamped via the IRAS, which is how the info is on the URA website.
Medical care is expensive and totally private in SG for foreigners, so any company provided cover needs to be really good, look at the procedures it covers, limits etc. Often the local firms cover is built around it being for a local employee who has at least some access to care/financial support publicly. Was lucky the company I was with provided a Cigna global policy, which I believe doesn't come cheap.
Cars are as we all know in SG expensive, if you are not aware and want to understand more, just look up COE prices in Singapore, that is just the starting point for car ownership, then there is the usual costs, plus extra taxes, road tolls and parking (not a lot of free parking in SG). But public transport is good and if needed there is taxis and grab etc. in the 8 years I was there I never had a car and never felt it was needed
Good luck if you want to give it a go, but definitely look at the cost of living in SG as a foreigner, as its a great place if you have money to spend, not so much if your living pay check to pay check.