Some amateurs give, as their reason for not operating portable or in public, the looks and reactions of other people. This is even though they're doing nothing wrong. In this video I address these concerns and give some tips on overcoming the fear of transmitting in public.
Interesting thoughts. One thing I have done to ease the portable operation is to use my vehicles -- mount the antenna (and optionally the radio) on the vehicle, and then drive to where you want to set up. It's another solution to many of the items you raised. It also makes it easy to move everything quickly if I want a better spot, or need more shade as the day goes by.
I gave up worrying or stressing over what other people think years ago. It's kind of a kiddie attitude. If people give me odd looks I say, "Curious? Come here, let me show you". Most people get it and ask questions. The only problem I had was living in the Bronx in NYC. When I had my HT with me one day at a local bodega, a rumor flew around the neighborhood that I was "Five-O". Was kinda funny actually, considering I look like the lead singer in Megadeth; full-on metal with very long hair.
I was setup in a park with my Yaesu 857-d and my trusty Buddipole vertical when two cops rolled up, hands hovering near their sidearms. Someone had reported a suspicious character.. me! I smiled, explained ham radio, showed them my gear and then gave them a demonstration. It wound being a great opportunity to demonstrate ham radio.
