My '03 26' has just a little play up and down (1/4"), but like 2" side to side. Roughly does the play fit the bill for a gamble ring or should I look to tighten somewhere else?

B1, 496 all stock 350hrs

thank you

The bolts in the top of the ring is a yearly maintenance item, they get torqued to 53 Ft Lb
With a 1/4 up/down you have some wear

correct hinge pins torque is important as well.

I would have to say prob 2 inches of swing and going to 53 ft lbs on the GB U bolt / nuts most likely you have gimbel ring thru the swival shaft wear. Very common especially when proper torque was never maintained - thats a 2 times min check / torque spec requirement. IMO that should be checked monthly when boat is in use and begin of boat season and end of.

The swival shaft nut is important as well as that loosens ---- more play becomes increased as well

Checked U nuts ant they didn't move at 53ft pounds. Can I get to the swivel nut? Or is that the one behind the sticker?

Should the drive be in any certain position when checking U bolt?

Gimble Ring

I know, I'm a dumb @ss

No, any position is fine
Edit: forget the any position, but cannot get to the top nut without removing the transom plate or cutting a hole

Thank you Dodge, I loosened and re tighten to 53 and didn't change. I guess I will address it over the winter when I re-power.

If the gimble ring will move vertical up/down 1/4", and also with the side to side slop, I'd suspect the c-bored shoulder that the upper swivel pin locates in the gimble ring has also worn, along with the square hole, as well as the pin, allowing the drive to drop down. Asses all the bad parts, cost to replace/repair those parts, and then compare to cost of a new transom assembly.
Went thru the same thing just 2 months ago on my cruiser. Was bettter off to just replace both TA'a so all was brand new, vs spend 3/4 the cost to rebuild the old ones and still have 1/2 the old parts.