Your right you can’t do both, get the grease gun on the fitting, hold it there and squeeze the handle. On my 2000 340 it’s a long way down there also. Given the only access is through the center removable ice bucket and drink holder.
I have a small grease gun about 6 inches long, uses screw on grease cartridges that are 4 inches by 1 inch round.
I fitted it with a 4 foot long hose extension.
That brings the gun up to just inside the opening and is just about the max length that you use and can squeeze the handle to pump in the grease that far.
So what I do and just did today in fact, is, I get my arm down to the bottom and connect the fitting to the grease fitting and hold it there. Which puts my face right at the opening.
My wife squeezes the handle 3 full times. It’s close quarters in there and she is just about able to pull the handle 3 times.
But it works.
If your seeing that it looks untouched….it is and was! You need to get grease in there. The manual I have says 3 squeezes of grease each year for that fitting. I’d double it this year.
And you really do need to grease the one on top, one under the compass and the worm gears under the compass also. Just remove the compass for easy access to that area.
And don‘t forget the ball joints (2) under the removable deck piece at the wheel.
They dry out and create a lot of friction when steering. There aren‘t any grease fittings on the ball joints and steerage arm but you can simply pack them, top and bottom, by turning the steerage arm left and right.
You can do the 6 inch access port. Just involves more work in cutting, fitting and sealing.
Try the long extension hose first, once you get a system going your only talking a few minutes of time in the pedestal.
Hope this at least gives you an alternative method.