Hi Big Red -I'm an older rider too,62 so I wear a helmet,I also installed a cushioned seatpost because long rides are starting to wear on my back.All my bikes (4) have self sealing tubes so I don't have many flats.I've had a few spokes break so I keep some spare wheels around.
My bike took me about 110 miles yesterday (160 cc Honda 4-stroke, 3-speed cassette in back) Average speed was 20 mph (stops, uphills, downhills, wind and all). So it was a long ride out and back. Hot too. I must remember to take water next time I ride on a 90 degree day. The real reason for this long ride was I wanted to know just how far a single tank of mid-grade gasoline would take me. With a 2.5 litre tank, right at 100 miles if I top it off before it spills out with cap. I had extra gas with me, for when the tank finally ran dry. My record run is 138 miles, made two years ago with a 66 cc HT engine.
Cushion seats are mandatory! I sit on a Cloud 9 11-inch wide. No residual pain after five and a half hours. I'd like to take on a 200-miler; maybe later this year. I still incur flats very infrequently now, mostly because of tube abrasion inside the tire wall or a tube manufacturing defect. Changing my tubes is time consuming under the best conditions. Along the road would take more time than I care. My "sag wagon" backup will come and get me, but I have to buy them a steak dinner treat.
To look "cool" is not at all on my list of riding desirables. I don't ride without helmet, jacket, etc. If somebody ever referred to me as "Dorkus Maximus", I'd simply remind them that I am older and more learned than they. I doubt that anyone older than a 57-year-old will make fun of us.
MikeJ