I admire your ambition but feel like you might be trying to do too much on your first trip. I'll be the first to admit I don't have a lot of backpacking experience but if you honestly want to hike in somewhere for 9-10 days, that is going to be tough. Probably more so mentally than physically. If I were you, I'd find a spot to hike in a mile or so and plan on staying there 2-3 days and see how it goes. Then plan on going back go the truck, regroup and resupply and then go from there.
Also, you said your one buddy expected to stay in a hotel. ALL of you will need to be 100% on board with what you want to do. If he isnt fully into the backpacking thing, you will be having issues by day 2.