just to close the loop on this:

Inbound, I caved and took the limo bus from HND to Shinjuku west exit. There's a lot more busses that head to the west exit only, and I didn't feel like waiting around another 30-40-50 minutes for a direct bus to the hotel. Note, if you haven't been, the Shinjuku west exit is within easy walking distance of the hotel - 3-4 blocks. I got off the bus at the west exit (spent a lot of time in traffic) and walked my spinner/backpack combo (100% on wheels) the short journey to the hotel.

I believe I could have easily taken the monorail to Diamon to Tochomae w/o too much issue and saved 1000Y and probably saved at least 45 minutes. But I'm also fairly familiar with transit there and the Shinjuku area, and I had a Suica card that already had 1000Y on it. But if this is your first visit, take the limo bus right to the hotel, I do agree with that. And especially if the weather isn't cooperating.

Outbound, Tochomae station for the Odeo line (platform 1) to Diamon, quick transfer to Hamamatsucho (elevators are available everywhere needed), express to Haneda, dropped right off at departures, done. Quick and cheap. Probably helped that it was Sunday morning but I'd do the same even at other times of the day - and there were plenty of locals doing the same, so it's not like it's way out of line.