I don't have a passport so I don't have to worry about traveling anywhere but the USA. I have never slept under a bridge. Typically I spend the night at churches, fairgrounds, town parks, baseball dugouts, store fronts/backs, pretty much anywhere I can find a decent overhang out of the way of the people. I go to bed late and get up nice and early. I spend time at a campsite sleeping, not wasting time. The amount of time I spend at a campsite not sleeping is measure in mere minutes, long enough to setup and tear down camp and that is about it. The rest of the day I spend riding or planning out the next day. I never have a trip planned out ahead of time. I plan from one day to the next.
In 2015 I rode all states east of the Rockies, and was in 20 state capitals during the 8200 mile bike trip. My set up works quite well. I did have a 32 degree down bag with me but I used it only a couple of times toward the end of the trip.
The mosquitoes in the midwest are not bad, at least not from what I have seen thus far. You stay away from water and stay away from grass and then bugs will stay away from you. Hence why I had a free standing tent with me and I always camped out on blacktop or concrete. I wanted to keep me away from grassy surfaces which give off dew overnight and make everything nice and wet. I never had to dry anything out, it always stayed dry since I always stayed off the grass.
Remember if no one knows your at the campsite then more than likely you will be left alone overnight and not have to deal with the cops or anybody else. Out of 75 nights out in 2015 I only had 3 nights where I saw the cops, the first one was because I was at a place I didn't want to be but I had no other decent choices around New Orleans other the river trial, national park property. The second time because I spent the night at another not first choice location thanks to the rain around the area making me move to a second rate location so I could have an overhang. The third time I was at the desired location, a church, on a Tuesday night/Wednesday morning. First time I ever had cleaning crew show up at 3:30AM. I only had the rain fly draped over me and the woman thought I was a dead body laying there
I didn't move when she pulled up either time and the cops and I had one heck of a good laugh over it. Other than New Orleans I didn't get kicked out of either of the other two spots, they checked my ID and left me head back to sleep.
Yeah, I have a tendency to plan my ride around the weather not around anything else. In 2015 I could have headed to my mom's house when I left Annapolis but since she was dealing with flooding which I knew meant plenty of rain was falling I instead looked at the weather maps and headed to where it looked like it would stay dry. I knew I would need to give it a month for the weather pattern to change and for things to dry out around her place so I spent 5+ weeks on the road before I ever made it her house, when in reality it should have only taken me 4-5 days to make it to her house.
When you have freedom, you have the freedom to change to your plans and not ride on a fixed schedule, no matter what happens. I enjoy the freedom because I know freedom IS free, slavery costs money. I spend very little money, so I can enjoy the freedom. Hence why the next big trip I do will not be by bike. Bikes costs too much money. Their is a cheaper, much sweeter way of traveling, which I have already did in the past, just not as extreme as what I will do it this time. I won't put up with the hassles of all the things which can go wrong by getting rid of all the things which can go wrong. Since I won't be doing 'big mile' days, even though they will be big mile days only in totally different context of what a big mile day is.
If you want a nice vacation why are you riding a bicycle? I thought cycling was work. If you are on a vacation you aren't suppose to work, you are suppose to be relaxing. Enjoying the hot tub in the hotel room, not hanging out at some stupid old campground in the rain.