Loaded question!!
If you have access to keep an eye on loads, it helps. That means not just what seniority but flying on what priority for new non-revr. We're fortunate to have 20 yrs BUT with that said, the valuable high priority passes we get--6/yr are reallllly valuable!
Consider you may want to look at connections sometimes--pick a secondary airport (particularly FL, sicne rental cars are cheap and no drop charges) My husband commutes CVG/NYC and flies DCA/LGA when he has few options. I've seen oversold flights@ -7 and we've both gotten on--maybe a connection airport--does PIT still work for that?

Flexible is the rule of the day! Hard to believe, but international can be a lot easier to fly than domestic!!

Presidents wkend---I personally wouldn't even attempt to ANY sunny locations AFTER the recent weather on the east coast.
If you make it--you will find it's a fabulous perk!

Regarding the chilluns--how old are they? I think it makes a big diff for some destinations if you're relatively new at this.
BUT--that said--make sure you get them to as many places as you can--while you can. Have fun with things like treasure hunts @ museums or city walks--like looking up a major item to find in the place--read about it first--then find it--each can have their own treasure to locate. Get videos at the library--they have an idea what someplce is like and then when they recognize it from the video--give them a little prize--shotgun seat or choice of TV--like that.

PS--you are out of your mind!! But have fun and be prepared to change directions. Gte the kids a good atlas and/or globe--they have one@ drugstores--it has touch control with a light (my walgreens had them for $10-15--dunno about this yr) I gave them to everyone in sight--better than Chia heads!!
Good luck and stay in touch with your travels. We're all rooting for you.