I agree whole heartedly with 'dadof6', you need better maps to plan better. I think that the time and effort is a wash between your idea to go to Long island Lake and dadof6's suggestion to go to Frost Lake. Both give you nice area to visit, but the Frost Lake route will take more time in portaging while the Long Island Lake route will mean more paddling.
Your third day is a concern and will require the better maps again. There are two portages between Cherokee Lake and North Temperance Lake (not one as you show). The first portage is rugged with steep ups and downs throughout. It is also difficult to find from the Cherokee Lake side. Think "look up" as there is a "landing" up the cliff about 15 to 20 feet off the water. This portage brings you to Sitka Lake. There is a short paddle and then another 108 rods of portage. This one is not as rugged as the last but still has some PUDS (pointless ups and downs) in it. You will welcome the long paddle on North Temperance Lake. The 53 rod portage to South temperance lake will seem like a walk in the park compared to the last two. You will need a good map to get through South Temperance Lake, with all the small islands you can easily get turned around. Then there is a 240 rod portage to a very short stretch of the Temperance River and then another 57 rods to Weird Lake (and the first campsite after S. Temperance on Weird Lake.) This is almost 600 rods of portaging. If you do the third day as shown, you will have almost 700 rods of portage to get to Kelly Lake. That's a long day.
You mentioned 9 people but did not mention how many tent pads you would be needing. Not every campsite will accommodate multiple tent parties.
Having not been to BWCAW on Memorial Day weekend so I have no idea how full it gets that weekend, but, generally speaking, the closer you get to an entry point the more campsites will be taken. Kelly Lake is within a couple of lakes to Baker Lake entry point. You may encounter some difficulty finding a campsite the last evening.
Having said all this, this is one of my favorite routes in the BWCAW. Cherokee Lake is beautiful and moody. I love the hills on North Temperance Lake. No better vista anywhere in BWCAW. The Temperance River lakes (Kelly, Jack and Weird are fun to paddle with the hills on either side. It feels like you have paddles back in time.
If you get to Gordon Lake, I love the ancient feel of this lake. It is primordial.
Get better maps and good luck!
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