tldr; don't make them ask; list some projects/work.
i can't fully understand part of your question, so i'll just riff a bit.
i'm braindead from zoomviewing all day. and dealing with aggravations that come with that.
i had one recruiter say today, "Is that unix, like U. N. I. X.?"
only mattered cause i thought i was talking to someone who'd been in the game for more than a day.
my next talk was with a tech founder of a streaming sql company, so at least i didn't have to deal that type of thing again.
my newly re-learned insights from this round of 6+ weeks of intensive interviewing are:
- have a story. what's the arc of your
'career'/employment/etc.? wtf _are_ you?
what do you _do_? what _can_ you do? what
do you _want_ to do?
- be able to tell that story in 30
seconds or less. 45 tops.
- know what you like about the job or
company you're applying to. or
pretending to like. that's at the
tail end of your story. as some
hiring mgr said today, "Why are we
here today?" Fuckin a -- i wish i
got more questions like that. we
could get shit done real quick.
- list any freelancing projects you can -
at least super-high level. this will
show you're not a lazy piece of shit.
not depressed. not ill in some other
way. etc. i.e. capable and willing to
do a 9 to 5.
like, you're gonna run across the gamut of people -- people who don't give a _shit_ that you're a failed wantrepreneur (or whatever you've been doing), and may even appreciate it, and people who can't stand you for it and will ask you some asinine question like, "There'a gap on your resume from v, x to y, z -- what were you doing during that time?"
bro, i literally can't remember what i did yesterday, much less 10 years ago, tf is wrong with you?
so, to me, resume-padding is just white-lying -- it's a social lubricant to get us through this hellscape called 'hiring'.
so, at what point should you stop resume-padding unemployment time?
at the point where have sufficiently removed the possibility of piquing the interest of a recruiter/hiring manager to the point where they have to ask you about it -- which serves nobody.
i've switched back and forth from telling my full employment story from the past two amazingly-shitty-for-me years -- a 2-year contract that ended after 9 months (thanks, Covid, but i was happy at first -- boring job), then a 3-month full time job i quit because i hated it. depending on the day or week, i've left out the 3-month gig -- it can be meaningful that I bounced, but eh -- if i wasn't completely miserable, i probably would have stayed for god knows how long.
good luck!