Wow, 8 months of exclusive expressing is a fantastic effort. Well done hun. That really is great work.

Unfortunately, as you know, maintaining supply while exclusively expressing is tough. It might be that the only way to maintain enough supply is to try the meds. However you could try expressing more often first if you can fit it in. Sometimes mums find that expressing for a shorter time more often is more productive than expressing for as long as they can but less often. Some other tricks to get more milk out while expressing are to put a warm compress on your breasts first, switch sides frequently while expressing (if you are not double pumping) and gentle breast compression while pumping. I guess you are already using a good electric pump.

To answer your other question, that is an individual thing from baby to baby and depends on how well they take to solids. Usually though, babies wouldn't drop to 2 feeds a day until after the 12 month mark. However, solids do replace milk, so as your little one starts to eat more solid food, the amount of milk needed will reduce. You might find that you can reduce the amount you give at each feed even if you can't drop one totally just yet.

As has been mentioned, there is a thread here on BB for exclusive expressers that you might find helpful. The ABA forum also has a very informative and supportive thread for exclusive expressers.