I bought a $1000 reliable bike, rode it for 8 months and realized that a reliable bike is very similar to Toyota Corolla, Ford Escort, or any other tin-can econo-box from the late 90's: boring. I drive an Escort Wagon, I wanted an exciting bike.
Financially I couldn't afford a newer "fun" bike, and even found some decent early 90's sport bikes for well within my budget.
Here's the kicker...new bikes are going down in price, old bikes are going up.
If you spend $1000 a nice Honda CB...chances are...you won't sell it for more than that. Any money that goes into it will be money that you won't get back. While it may seem reliable, its all the "fun parts" that get expensive. I've seen tons of good running, cafe'd, clip-on, get-yer-chuck-taylors-and-ride kind of bikes...but people have already done the work and want good money for them. What's the fun in that?
I bought a $500 basket case that I knew ran, had more money in the exhaust than the whole bike, and had a new set of tires. Most of the expensive stuff was already fixed. It just needs love. Love is free. Love is cleaning the carbs, buying new jets, setting the timing, cleaning up the wiring harness, etc but when its done it won't be a bike that somebody else threw parts at, it'll be my labor of love.
My opinion? If you want to ride a motorcycle, buy a Ninja 250 and ride.
If you want to involved in motorcycle culture, in "cafe racer society", in restoration or stylization of old bikes, then buy the cheapest titled bike you can, and then buy a few more parts bikes.