OD drain ? not sure. The water that came out was a little milky. Also worth mentioning is the fact that outdrive went back down on its own, it didn't stay up.
The outdrive oil drain screw is situated at the lower front of the gear housing, looking at it from the prop end its on the left. I think the suggestion is that you check the drive oil in case you have water intrusion.
If you had the drive down and the water came out after lifting it, I actually think it may have been excess water lying in the housing and may have exited via the drain hole which is in gear housing the opposite side to the drain screw but just above the housing were the prop shaft sits.
Either way, I think the two issues may not be related.
One theory about the water being milky could be that your lower shift shaft seal is leaking but you would likely have a drop of oil coming from the drain hole as well.
First thing to check though as suggested is to look at your outdrive oil.
Back to the rams and hydraulics. I wouldn't have thought you would be able to lift the leg if the rams are working properly. First of all check the hydraulic reservoir on the trim pump, if its foamy you may have air in the system or if its low this may be your problem. You can purge the system by undoing the fill cap and fill to correct level then raise and lower the leg 6-10 times.
Check these items first. Hope this helps.