Depends on the model of your saildrive. On our 120S-E it is definitely not possible to get the tube to the bottom of the leg, as there are two sharp turns and nothing to guide it through there and into the bottom half.
On later (130+) models it may be possible to get the tube down into the leg, as there is a more direct path, but even so you'll not reach the absolute bottom. The saildrive is not like an engine, it has no oil filter, so any debris will collect in the bottom of the leg and can only be properly drained with the drain screw there. If the debris is not removed, the inner seal and prop shaft will wear faster.
Removing these particles is really the only reason for doing an oil change in the first place. Therefore it is of little benefit to doing a partial oil change from above. Just haul out next year, drain the oil from the bottom drain plug, check/replace seals and inspect the shaft for wear.
On our saildrive, the drain plug should also have a small magnet, that gathers any fine metal parts (from wear) and prevents them from rapidly wearing seals and shaft.