Read everything that has been said so far, there's a lot of wisdom in these posts so try to absorb it all.
A lot has already been said that I would have said so I'm gonna to try to keep this basic:
There is a difference between Vintage intruments and Expencive instments, I've had both I would recommend new items, specificly high-end items buy cheap brands or low-end items by expencive brands (e.g. a $500 Squier would probably be as good as a $600 Fender). Personally, I would recommend a high-end Epiphone or somthing in the $600-$1100 range.
Find somthing you're comfortable with or like the shape of, if you don't like the sound you can always mess with/replace the pickups (however I wouldn't do this with a vintage instrument).
Put some money into the amps too because you'll always use your amps & effects (bands that used rally cheap guitars or smashed their guitars usually put more money into the amps to keep a good sound too).
Vinatge Les Pauls can be heavier than a Strat by a lot, a regular Strat usually weighs 6-8 pounds a Les paul can weigh 8-11 pounds or even 12 pounds like the Les Paul I got.
Don't tour with your expencive guitars! thats just what the cheap ones are for, I would recommend puting some money into your cheap guitar or getting a new one for live preformances, while roadwear can be attractive sometimes 9/10 times it's not. Insted record with your expencive guitar and preform with your cheap guitar.
Also: can we see some links for a listing if there is one?