I hate boots, but I want to like them.

I have had 3 different pair of cheeper boots, and Im never happy with them. And so, Im not very experienced with boots.

My goal is to find light weight, flexible sole, water proof, high comfort boot that feels like a "tennis-shoe" (or more specific a skateboarding shoe)

Redwing boots is what I have been looking at now. I think they are the most promising prospect (unless someone else has a better suggestion)

SO, THE BIG QUESTION IS, insulated or un-insulated.

insulated version has 400g of thinsulate.

my hunting conditions will include temp range from 70 degrees F to 20 degrees F damp and windy.
sandy conditions. rocky conditions. lots various burrs and anything the desert can grow to poke you.

I am afraid that the insulated version might be too hot on warm/hot days.

Some people have told me that insulation is helpful in cold and irrelevant in the heat. Is that true?

I need the opinions of those with more boot experience

1. I now see the wisdom and merits of much older generations.
2. Technology makes things cheaper, easier, and less labor intensive, but not necessarily better.