I started up a VPS a month or so ago, and I am extremely pleased so far.
Having a VPS gives me flexibility far above that of shared hosting, and the price is quite reasonable. I've always wanted a VPS, but I never dreamed I'd be able to afford one.
One thing to keep in mind: You'll be bewildered for a while, trying out various options on your control panel. You'll create a new FTP user, say, and after you click the button, you'll get a cheery "done!" message, and you might shout at your computer, "No, we're NOT done! How do you log in? What's the password?" Never fear, within about a minute you'll get email from Dreamhost with all the details you're worried about. That's the one thing I had to realize before I could begin to relax.
I've dealt with hosting companies that were okay, some that were not all that great... and some that were incredibly, colossally abysmal. Dreamhost is not perfect, but it is the best I've dealt with so far.
I'm a long time UNIX guy, so a green text screen and a Linux command line interface gives me warm fuzzies. Your mileage may vary.
I'm still prowling around my control panel, opening up menus and exclaiming "Holy crap! I can do THAT? Awesome!" The best thing of all is that my VPS is FAST. I have it on the lowest memory setting (I may bump that up someday, but not just yet), and it's 10x faster than my last webhost.
I have a complicated, homebrew PHP website, so it took me around 2 weeks to get it ready, mostly refactoring the code to make it more efficient and removing a lot of crazy code I used to get around bugs at the old host.
My website users are ecstatic with the new site and the performance, and I'm pretty excited about what I can do in the future.