What I think is that the original poster should first stop thinking about where they will stay ever night. Then stop looking at weather reports. Learning to trust your gear takes time and will save you money and stress. I have been on a continual cycling adventure since 2011. The first days out was nothing but wind, sleet, rain, and snow storms. It was not fun. I was angry and wanted to quit once I realized I had only gone 30 miles in ten hours. I called a friend and went to his house after realizing I was only down the road. The next morning I wanted a ride home. He laughed at me and said he was going to work and I had got to get myself back. It was below freezing outside. He made me sitoutside so he could lock up the house on his way out. I sat there in his driveway from 5:30 a.m. until 8 a.m.before sucking it up and heading south. The weather was a butt all the way from Washington DC to Hampton, VA. Then I got hit by a truck days later crossing from Virginia into North Carolina. I turned around and backtracked to Williamsburg, VA before finally getting on track for Florida via another route. But after several days I developed the mindset of looking foward that each day will be better than the first. If I waited it out in a motel or better yet, started on a nice forecasted week ahead- each day foward I would be fearing the day it got worse.

The toughest part of cyclotouring is knowing when to stop and where to sleep, in my opinion. Unless you are in the desert.... not dessert, then it becomes water and shade. But I think we all get what I mean. Sometimes we stop when it is not neccessary and that is okay. The trick is to learn when to actually stop. Only you can decide that. Also, I realize you may not have the "street smarts" degree which I have, but seriously.... never pay "the price" for a motel. Be honest with the desk clerk at the inconvenience of the situation you are in. Cylcotouring is about people and experiences. You may be surprised how important meeting you can be to someone feeling stuck in their own situation. Keep that in mind as your tough days roll away. Remember, generally, when it is raining out there are less cars on the roadway.