I'm past the Boat and off the resort island. I got stuck on the island because you have to dress up as a a lady in a bikini to sneak past the KGB which involves stuffing your bikini top with the wad of dough.
As you are aware, the game is command based, so syntax and language are fairly restrictive. I used a couple commands along the lines of, "stuff top with money," which results in a response of, "Nah, you better not." Leaving you thinking that you have the right idea but you're using the wrong inventory item.
I eventually realized I had the the wrong phrasing. "Put money in bikini top," worked but you also have to be off screen to accommodate Larry's "modesty."
It's all fairly obtuse. Larry 1 received an early "remaster," that turned the game into a point and click, eliminating the command element of tha game. It was quite a bit more accessible but ruined a lot of the "logic" fun IMO. Larry 2 and 3 never got the same treatment as far as I'm aware.