Booked my wife and I on separate tickets from JFK to SXM (only 1 X fare left, so by ticketing separately we saved a few bucks instead of both ticketing into T). Our rule of thumb on upgrades is that we'll take whatever we can get (i.e. we'll separate if only 1 seat up front).

Should I ask Delta to link our record locators as traveling together? Or would that cause us to get skipped over for upgrades if only seat is available when we get into the upgrade window for clearing in advance?

We're both DMs this year, if that changes the answer?
Next year, I'll be a PM and she'll be SM.

I guess my question is broader than just upgrades. Curious about overall strategy and pros/cons in the future re ticketing together in same locator, linking linking two locators, leaving unlinked?

Linking will not affect upgrades. You'll be upgraded separately at your own priority level. It's only when you are booked on same reservation when the system may not upgrade one without the other (and your companion inherits your upgrade priority level). For a PM and SM, you would almost always want to book together on one reservation and only consider splitting if there is one seat left.

https://www.delta.com/us/en/skymiles...llion-upgrades

If you and your companion are in different paid ticket reservations that have been linked, upgrades to U.S. 50 domestic Delta One, First Class and Delta Comfort+ work a little differently:

• For domestic Delta One and First Class, your upgrades will clear based on your individual Member Status and confirmation windows, if available. For example, if Platinum and Silver Medallion Members are traveling together, the Platinum Medallion Member will clear at the Platinum window and the Silver Medallion Member will clear at the Silver window. If your companion is a General Member who does not have Medallion Status, their upgrade will clear no sooner than 24 hours prior to departure.