hi Ko_ko_ko
my situation is/was similar to you.
my post graduation permit was expired after months waiting for AOR and i lost the chance to apply for BOWP.
But after tons of research, i found many people who succeeded receiving the BOWP, without AOR , on implied status after they work permit expired.
it took between 7 to 10 days for them to receive BOWP after they got the AOR.
so i applied both restoration of status as worker and BOWP a month ago and i just got AOR last week, so im still hoping a good news soon.
but i think things are positive since they have not rejected my application for extension already.
technically it's not our fault AOR is taking more than 5 month and should not be the reason we lose our job and status
it doesn't matter how many time you got rejected, I don't think it will affect you negatively in the future.
if i were you, i will apply both today.
there is option to upload explanation letter and write a long and nice letter to explain your situation and your plan if you stay in Canada (just bonus)