Hi, for the most part you can get to all the different lakes on the chain via your boat but some areas you will need to raise up the moter so you don't scrape the skeg or damage the prop.
Late summer is a great time for fishing on the chain, the weather is usually warm to hot and the panfish and pike along with musky are the big biters at that time of year.
Trolling is permitted on the michigan lakes, but not the wisconsin lakes. Make sure ya check the regs for the boundry water lakes.
Thanks for the questions and I sure hope ya have a fantastic time up here