I listened to my gut and it has paid off. Yesterday, I finally booked a one night hotel stay in Boston on my way home from Iceland. With the flights I have, it is impossible to make it home the same day.
Normally I would have had it done when I booked everything else back in January. But I just couldn't pull the trigger for this one.
I had found a couple of hotels that would be suitable and were reasonably priced. My rule of thumb for long travel days where I'm going to be exhausted is I will pay to be in a nicer environment especially if I will only need it for a short period of time as to ensure as much as possible, I will get some quiet rest and good food.
What was tripping me up was the shuttle service/ride to these hotels. I know I wouldn't feel like calling them up. Also in the morning, it usually means I add another hour to make sure I get back to the airport in time. I really wanted to be in the hotel that was attached to the airport so I could just walk but didn't want to pay $250US.
Something told me to check yesterday and for some reason, the advanced prepay rate had dropped to $119US. I took it and other than the transfers from Keflavik airport to Reykjavik, which I plan to buy once I land, I am pretty set to go.