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I don't think you'll find many telescope experts here, I'd reccomend you go to a reddit subreddit about telescopes and post there.

Scratch that, if I were you I'd post it here : http://www.reddit.com/r/AskReddit/

Clicky

I'd say look for stars >.>

To the Moon!

Boobs. Definitely.

Aliens.

Look for Wheatley.

Start by looking up.

When it comes to a specilized/niche product I really think it's best to ask the right people for advice; really don't know much about telescopes and the community that revolves around them but this seems like a good place to start your searches: http://www.cloudynights.com/ubbthreads/ubbthreads.php

I highly doubt you'll find here (or on reddit) many people that know what they're talking about when it comes to this matter.

The most important thing is definitely aperture size. Also, eyepieces under 10 mm are kinda useless usually.

Through your neighbor's windows and hope to catch them changing.

For that price i'd go for an 8" dobsonian...

if you like computers too you might want to check this out as well : http://milkyway.cs.rpi.edu/milkyway/ or http://einstein.phys.uwm.edu/

Here some pr0n for you.

Also check some specialized websites not just amazon etc ( astrosmart, cloudy nights... )

Waldo.