Holy cow, this is a dope thread. I'm ~jmhodges! Seeing so familiar names in here is surprisingly moving?
Professionally, I do software consultation and run a small web service. I got to jump through a cloud illegally a few years ago! I recommend it![1]
Also, I think dogs are cool[2].
[1] While, sure, it's illegal to parachute through clouds in American airspace unless you're in military exercises, you can do it too with the technique I discovered:
1. Charm the gruff but kind Navy vet you're strapped to by talking about how your dad was Air Force
2. Ask him about his experience training Navy and Marines in how to fall out of planes.
3. Mention that sometimes your dad flew planes you were riding in and how'd you'd look out the windows and wish you could touch the clouds
4. After popping the chute, and he directs you to "pull hard on the left" you may start to form some questions about where you're going but -- this is crucial -- pull hard on the left line before asking them. It's unlikely you'll be able to finish any interrogative thought for a few moments more, anyway, due to the recurring realization that you were just face first towards Earth with miles of nothing between you and it
5. When he says "reach out" over your repeated "thank you. thank you. wow. thank you", take one hand off a toggle and make a fist in the vapor as many times as you like. Take a moment to notice that the inside of a cloud has plenty of light to see and is only very slightly more grey than the outside.
I hope this helps.
[2] They really are.