My situation as of now -
I recently got my PEP approved, with the IPA stating a deadline of early September (i.e. I have to use it by then else it lapses). I am on garden leave with my current employer (made redundant as part of global layoffs), with my last paycheck looming in the next few weeks, after which I will be officially "unemployed". Following termination of job, I will go on to a 90 day STVP as per my HR.
I'm actively interviewing for jobs in Singapore, but it's not a great recruiting environment, especially in my industry (non-tech, but there have been a lot of "silent mass layoffs" across many big players globally).
I've a couple of questions which I'm hoping to get some clarity on:
(1) How does the 144K minimum salary requirement work if I were to start a new job only in end 2023, and I've not been drawing a salary between June / July and then? I'll be reaching out to MOM on this, however thought I would check in with you all here as well.
I looked up past threads, came across this one (viewtopic.php?t=149862) with some helpful comments from SundayMorningStaple.
My understanding from this is that as long as I take up a job @12K per month minimum whenever I start (in say Nov 2023, so only 2 months on PEP in 2023), I would still be eligible to retain my PEP, even though the total base salary for 2023 (current employment on EP till Jun/Jul '23 + future hypothetical job on PEP starting Nov '23) may not meet the 144K minimum requirement. Is that correct?
Or would MOM expect a total comp of 4 months (Sep to Dec) * 12K = 48K regardless of when I actually start a new job? PEP start deadline in IPA is Sep 2023)
(2) Taking a step back, I am also wondering when is the best time to "activate" my PEP even if I haven't landed a job offer.
I am inclined to do so as late as possible (i.e. close to the deadline in PEP IPA), however is there any advantage to taking it up sooner, even though I may not have a firm offer in hand?
(3) There's a small voice in my head that also suggests not using up the PEP option at all if I don't secure a job offer by Sep '23.
With the dwindling job prospects and economic conditions, I have started to expand my search outside Singapore as well. This would mean that I leave Singapore by Aug / Sep, and if I were to ever get a job offer back in Singapore at a later date, I can come on EP and then utilize the PEP option if I meet the salary threshold. While I realize that the threshold goes up, it's not unheard of for senior executives in my industry, especially if I get a few more years of experience under my belt.

I'd love to hear thoughts from other forum members - what have they done and / or observed others do?