My starboard drive leaks off and drops to full in position.. What would be the first thing to look at or what would be the things to look for to repair this issue?

First thing would be check the fluid level in the trim pump. If it's low inspect the lines and fittings for leaks. Check if there is a puddle of fluid in the bildge. If there is fluid in the bildge then raise the drive and then watch for a leak to start sqirting out of one of the lines as the drive falls.

How fast are you talking about? If there are no leaks and the pump reservoir is full then it's probably a valve in the pump.

No leaks and it takes days for it to come completely down.. is this valve something that can be repaired or is the whole pump need replaced?

To tell you the truth I wouldn't worry about it if it takes days to come down. It's recommended that the drives be down any way when not in use to keep the bellows closed.

There is no information in manuals and no parts availiable to repair/rebuild the valve bodies on the trim pumps.

You can buy new or reman valve bodies though.

The hydraulic valve bodies have 3-4 check valves which require adjustment to be made during assembly on a bench with the necessary gauges and equipment to perform this. It's not a DIY thing.

Do you know what pump you have?

My trim ram is leaking it needs new seals. It does not trim up as fast as the other drive.

There the newer style with the plastic resevoir! My K planes have the black canister style.. I never raise my drives past 9 on the indicators, the boat sits so high on the eagle trailer I tow it with the drives down, I'm not worried about the bellows because I have the block off plates..

I was refering to the bellows on the drive shaft/u-joints. When the drive is up/out the bellows is streched open, especially in the trailer position.

DUH!! I don't know what I was thinking.. Yea I always heard that it wasn't good to keep them up!! I'm just worried that when I'm running that the drive will creep down at a faster pace, and that I'm gonna have to keep bumping the trim up to keep it at the correct trim angle..

If its not leaking externally then the issue is in the valve body of the trim pump. Had the same thing happening on my original trim pump, replaced it with another one and no more droop.

Ultimately you are going to have to find out by running it. However I can't swear this to be true but I came to a conclusion that extra force pushing down makes the valves hold better. With my boat on the trailer parked I would raise the drive a little so the skeg wouldn't be on the ground. It would always bleed down with in a day. However when I have it raised in the trailer position and the drive is standing almost straight out making much more down force it will stay there forever. I tested this theory several times and always came up with the same results. With indicators you should be able to tell real quick if it's not holding.