Weighing retirement options

I'm obsessed. With dates and retirement math. 

The potential dates for my retirement are approaching landmarks, and I dither about timing my exit for the best pension outcome. I vacillate between Factor 80 or Factor 90, which would be reached just 11 months later. I reason I can tough it out for an extra year for a bigger pension, and then desperately hope I can stand working even a few more months without quitting prematurely or being unexpectedly laid off before I hit the qualifying dates.

My latest puzzling is adding the government Transition Exit Initiative or Voluntary Exit offer program into the mix, and then calendarizing the work-back dates for Factor 80 or Factor 90. (Date X - 6 months - 19 weeks - accrued holidays would make for the last day in office Date Y). Wondering... will the government keep the incentive programs or axe them? Will my manager approve if I apply? With TEI or VEO taken into account, even Factor 90 might be a possibility before the end of 2021! But do I want to retire when there continue to be all these Covid restrictions on travel and activities?

Then come the dates on when to take Old Age Security or Canada Pension or start cashing out RSPs or TFSAs. Wondering..... How much should I let the OAS clawback dictate when to start CPP? If I live cheaply abroad for a few months each year will that save money overall?

I play out different scenarios financially but it is all quite confusing. Retire on Factor 80 but start taking CPP? Stick it out a few more months for Factor 90 for extra pension dollars, but start CPP while still working to stash into RSPs for later? Of course I want to maximize for the best financial return, but the additional dollars, while nice, really aren't going to push me into another tax bracket.

Previously I've asked to run the numbers with my financial planner re Factor 80 or Factor 90, and her take was simply, if you're not loving your job a couple extra thousand isn't going to make much difference. Whereas I think, hey, that is renting a cottage for a week or two, or taking a trip to Chicago. So while I may not be loving my job most days I don't really hate it either. Being able to work from home has also made most days infinitely more tolerable.

I think my obsessing with these numbers is a way to try to make retirement more tangible and predictable.

There are big unknowns. Some things are in my control, and others not. Dates of death, levels of wellness and health are huge factors for life in retirement years, regardless of pension schemes. 

You can make all the plans you want but there are no guarantees.