I agree with what the folks here have said and what Dian posted in Health. All of this has got to feel a little weird because all of your experience with PZI and your knowledge about its use along with your data is yesterday's news. Every time you think about adjusting dose based on the pre-shot value, stop and remind yourself this is Lev, not PZI.
You are also correct in that until you have more data, you probably don't want to shoot a dropping number. It also depends on where that number is dropping from. If it's a yellow or a blue, that's better than shooting a green that's on the way down. (I shot a dropping, low green once and I don't recommend it.) It's also fine to shoot if you know Tom is surfing. Again, if he's surfing at 50, you probably don't want to shoot right now. It all depends on the particular situation and what you know about your cat on Lev.
FWIW, I think you would have been fine to shoot the 233. If you look at the Data Ready sticky, we will often tell newbies to not shoot below 150. If you want to set the "wait and see" number at 200, that's fine. You were well within a margin of safety to shoot at 233. I'm guessing if you'd waiting an hour, you would have caught the rise a bit earlier. (FYI: If you shot on the 285, that's the number that we put in the PMPS slot. Your AM shot time will be 12 hours from when you gave your PM shot. Right now, your SS is a little confusing since you have a green 13.5 in the +1 spot from last night.)
Right now, if you can concentrate of building up enough data so you have a solid understanding of where Tom's Lev onset and nadir are and what kind of duration he gets, you will be doing a lot to build your comfort level.