Hi Jeremy. About your tripod, I don't know. I can't really tell you since I don't know exactly how/when/where you want to use it. But I don't think you'll run into much problem. It's always good to be polite and ask first, and that's probably all you have to do.
I think the toughest hurdles you might experience in Japan is probably when you try to take out cash from ATM, you might find no English menu on the screen. Outside of Tokyo, that's common. Indeed, a lot of ATM machines (especially the ones in convenience stores) don't take foreign ATM cards. So, just bring a VISA or Mastercard in case and have enough cash(yen) ready wherever you hang out and stay. That's all.
Starbucks is everywhere if that's also one of your main concerns. Don't worry you'll probably find one there.
About your chance to run into English-speaking people, I give you an idea: Even in every rural community, there's at least one or two English speakers teaching English in public schools. You'll be amazed when you see them.
I've been to Takamatsu once. It was late last summer in the aftermath of the hard-hit typhoon. I was a disaster-relief volunteer and spent two weeks working with the locals. Although it was an extraordinary time, I think I managed to get along with those people pretty well and took pictures on the side.
Takamatsu, also known as "Sanuki" region is famous for making thick udon noodles as its traditional style. There are many noodle shops, and they are all good and cheap.
Also, the city of takamatsu, according to the local men, is a mecca for erotic bath houses: t has a high reputation for pretty girls. I didn't explore in that area, so I can't really tell you much about it, but it's a big culture there.
But one thing, seriously you have to be aware of is that one of the nearby islands (I forgot the name) has a facility for leprosy (we call it, "hansen-byo") patients and is known for that. Those people come to Takamatsu on some occasions. They live in the area. I don't know if you can tell from a distance because most of the time, they hide their faces or put makeup to cover up what they don't want you to see. So, just be aware that you'll be in that area with your camera. It's a very sensitive issue because they have suffered from the discrimination in a long history, and they want to keep their privacy protected. I don't know if your Lonely Planet tells you this or not.
Meanwhile, there's an island called, "Shodo-shima" which is only a short ferry ride away (about an hour) from the Takamatsu port. I would say, it's a Japanese version of Martha's Vineyard (in a way). It's not big for tourism, but it's pretty. A couple of films were shot there.
Anyway, have a safe trip to Takamatsu. I'm near Nagoya (and Kyoto), far from where you'll be at, but in case if you need help and/or reach me for something, send me a personal message here.