Route Planning - I need advice and maybe a reality check?

[East Side Hiker]

If you've been doing what you've said for your whole life, and you're in shape, I would think you would have a nice adventure if you're cautious. Can't you squeeze in one more day? Then it may not seem so ambitious. You might find yourself with your head down looking at the ground. But then, many of us do that frequently anyway... (unfortunately).

[East Side Hiker]

At least you're thinking about it and asking questions. That's a good start.