Thank you for the quick reply!
Ok, so lets sort things straight:
It will be just me.

If you say some places are going to be closed due to bad weather (snow is not an option for camping for me unfortunately, I don't have the gear for that), I won't do them. This is one of the reasons I put this post on, to figure that kind of stuff now.

Let's say the trip will be from Very late september/the very beginning of October. What places that I listed will have fine weather to be at?

I have until November 20th (it can be shorter, but that's how long I've got for it), I think it's more then enough, but you tell me. I'd like to spend couple of days at each place, not to rush anywhere. November is already winter, this is why I thought to "finish" with the cold places first, so I can go to the warm places later ahead.
The thing is, I NEED A ROUTE.. That's something I really need help with.

Gear- I have a regular sleeping bag (I know it's not idle), and haven't got a tent yet. If you have any recommendations about a tent, it will be very helpful.
Clothes- I have short clothes but I don't think I have the clothes I need for cold weather, if you can suggest on that subject.
I have a great 75+10 Backpack that I trust and it has raincover. and I got hiking shoes I can rely on.
Any more gear I need to think about?

Thank you so much, I know it takes time to help, I really appreciate it.