I know you didn't say it. I'm saying lots of people say it. Specifically, I said. . . And. . . As I said, there is lots of nonsense bandied around on the internet about living in Thailand. I'm addressing all this nonsense, such as people saying it's so much more work, when it isn't. Regarding your wife having to attend, there is a 30 day window to get your renewal application submitted, and I'm pretty sure there is flexibility from immigration where illness or incapacity is involved. I already outlined the reasons someone might choose to extend their stay on this basis i.e. it counts towards PR/Citizenship, and allows you to get a work permit if you choose to. These are not minor considerations if you're serious about living in Thailand in the long term.
I'm saying people use the horn in other counties too. Horns aren't something they only put in cars assembled in Thailand. Actually I have no recollection of getting the middle finger in 14 years in Thailand and I sure drive a lot here. Flipping the bird is a western thing, not something you see Thai people do as far as I know. Maybe some younger people do it if they saw it in a western movie, I never saw it myself. . . See what I mean? Confusing culture with lackadaisical law enforcement, it's a very common mistake for farangs, it's discloses their immaturity, not that of the Thai people. Most Thai drivers want to get home to their families in one piece. Nobody in Thailand wants to be ripped off by service providers. . . but when dealing with the frustrations of living here, it's easier for most foreigners just just say they're all idiots. I've pulled this thread off topic, maybe start a new one.
Strongly suggest you start by contacting MoM (Ministry of Manpower) as though the minimum salary to support dependents (in this case your parents rather than your children) is s$5,000 pm, Malaysia & Singapore have a special relationship so there may be different requirements. As for "How Much", it all depends on what standard of living you're looking to have but could comfortably rent a 3-4 bed HDB for s$2,000/s$2500 pm & food/transport is not that expensive however schooling can be but that's another area to check to see if there are any special arrangements for Malaysians. One other approach which is becoming increasingly popular with people working in Singapore is to move to JB & commute daily/weekly, as you would have e-gate access at immigration on both sides, it's relatively easy to do.
I never said the extra requirements were onerous (though the "change over" may be & there may be people who's spouses may struggle to attend immigration when required due to work commitments or illness), I simply said that there were additional requirements. I would be interested in hearing about the "additional options in the future family extensions" do you have any more details?... But a quick Google shows that though you can skip the PR stage... "If living in Thailand for “reasons of humanity” such as being marriage with a Thai people or having a Thai-born child or having graduated from a university in Thailand, he or she must have an income of at least 30,000 baht a month and be able to prove that he or she has paid taxes in Thailand for at least three years.", so obviously if this is a goal for the OP then the retirement visa is completely inappropriate. Edit: For clarity, the Retirement Visa is inappropriate as the OP needs to be working/have a work permit during the PR or Citizenship application & so by definition is not "Retired".