What should you look for in a decent used Motorcycle?

I'm looking for my first bike, fresh off getting my endorsement and I still have the bug.

Love the Honda Rebel 250 that I trained on, but was told for a guy my size (heavy) I should go no lower than 500cc. I've risen 250's and 500's mainly sport bikes (crotch rockets) before and those are fun but I think I'm more of a cruiser… Love the Honda Shadow, love the Vulcan look that type of bike.

I've been searching online, and on Craigslist for specifics but I'm not sure what to look for as far as what makes a good used bike worth buying. Limited funds and don't want to buy something that will break down on me the moment I get down the drive way.

1. Is mileage on a bike the same as a car… I.e. Bikes around 46k miles is that good, bad, normal, average and should I look at something else.

2. I read somewhere that custom paint job screams crashed bike is that accurate?

3. How can I tell if the engine, throttle, clutch, chain and the other important parts have no issues?

4. If i do buy say a Shadow, or a Vulcan with a bad engine/throttle/clutch/chain/etc on average what am I looking as far as price to get it fix or replace it (ball park)?

5. How can you tell if you are getting ripped off on a used bike?

I don't care to much for scratches and dents but obviously with those its been put down so what should I look for as far as making sure the bike is good and worth the buy?

Can anyone clue me in?

In a nutshell, I will answer everything:

If it "just needs carb work", "just needs a battery", "ran last year", walk away.

Bring someone who knows bikes, not your buddy who has a sweet Ninja that he got last year, someone who has a couple hundred thousand miles riding experience and knows how to maintain a bike.

In short, buy a running/driving bike. If it needs anything, it points to neglect, walk away.

#1- It isn't mileage, it's maintenance. The better the better.
#2- Maybe, but women color their hair just for a change.
#3- If you can't tell have someone that KNOWS do that job for you. (you'll learn or keep paying).
#4- The sky's the limit, that's where #3 comes into play.
#5- See #'s 3 and 4.