I firmly believe that any audio enthusiast who is just starting out, or who has high end taste, but a limited budget, should start his or her audio journey with headphones. You can get GREAT headphones for $1000 or less (often much less). But more than that, the most important thing any audio enthusiast can do is to learn how to listen critically. Also, all the best speakers and amps in the world mean nothing if you have bad room acoustics, or you live in a situation (apartment, shared house) where you cannot listen to your system when you want to, and as loudly as you want to! Headphones are not restricted by the limitations of your room or living situation. So start there, learn how to listen critically, and save up for a house!
And while you're saving up for that house, you're enjoying your headphones and planning, planning, planning. What do you want your future home theater to be like? Do you want a cozy, 3-seat couch theater? You can turn any room that's about 12' x 15' or larger into one of those. That could easily be a spare bedroom or a den. But maybe you want a theater big enough for guests and extended family. Maybe your want two or three rows of seating, or to fit 5 or more seats across in each row. You're gonna need a much bigger room for that. Probably a basement recroom that you can close off and make into a dedicated theater. Or maybe you want the proverbial "Man Cave" with a pool table, card table and bar all built into the shared theater space.
Point is, plan ahead so that you know what you're looking for when you go to buy your house. And if you know what sort of theater you're going to build, you can start to think ahead about speakers and subwoofers that will be appropriate for that size of room, and the sort of amplifier power you'll need in order to drive them. The room dictates the gear. The room tells you where your seat should go, which tells you your viewing distance, which tells you what screen size you're going to need. It's really all about the room. People so often only think and worry about the gear. But get your room first! The room is everything!
In the meantime, get great headphones and enjoy

. The biggest regret any of us has is buying gear that we think is going to make us happy, only to realize that our circumstances don't really allow us to use that gear the way we want to, or we bought it thinking we'd move it to a new home in the future, only to discover that the new home has a room that demands different gear than what we bought! The absolute best thing that you can learn is how to wait, hold onto the money you have, and only spend it when you're truly ready and the time is right. We've all let our excitement get the better of us at some point and sprung for equipment that we were just "sure" we'd get real use of some point in the future. Well sometimes, that envisioned future never comes, and that purchase just ends up being a waste. So plan all you want. Dream all you want. But keep your money, wait, get the house and the theater room you want first, and then spend your money on the gear!
Also, don't waste time trying to save a nickel when you can use that same amount of time to earn a dollar. All the crap people do with clipping coupons and looking for sales and deals. Instead of the amazing amount of time people waste doing that, head on down to Labor Ready and dig a trench or haul bricks for a day. Get a second job flipping burgers or walking dogs. Don't let pride or the idea of "relaxing and living the life you want right now" allow you to get lazy or turn down some easy money that's right there for you if you just put in a few hours of honest work. While your friends are teasing you for working a crappy job while they play Xbox and get high, in a few short years, you're putting a down payment on a house and driving a car that's paid off, while they're still living in a crappy rented apartment with 3 roommates, and bumming smokes off of their ugly girlfriends
All the while, you're enjoying your headphones. Never bugging anybody else, and being able to block out the noise of the world whenever you want!
The best deal in the world right now, IMO, is to spend $100 on a pair of Shure SE215 in-ear monitors. They're amazingly good for the money. And as versatile as it gets! Get the optional iPod/iPhone or generic phone/portable player adapter and you've got a superb portable solution with a control button and mic. Plug the SE215 into your computer. Plug 'em into any type of portable player. And if you want something closer to a surround sound, home theater experience for movies and TV, get yourself an
Astro Gaming MixAmp . For $130, you can plug in pretty much any source via optical, stereo RCA analogue, or mini line in. The MixAmp is a full on Dolby Digital 5.1 decoder. And it uses Dolby Headphone processing to create the sense of 7.1 surround playback. It's a great way to bring a solid headphone amp, DD decoding and connection to virtually any source to your wonderful Shure in-ear monitors.
The SE215 themselves are clear, accurate, and they've got a bit of a boosted bass end for really kicking' music and some pretty amazing impact with action movies and LFE. They're accurate and transparent enough for you to learn how to listen critically with them. They're also very durable. They're small and super easy to bring anywhere. They don't "leak" sound at all, so you're never bothering other people when you're listening out in public. And they do a darn good job of blocking out noise from the outside world, just like earplugs.
Of course, if you want tremendous fidelity, the kind of transparency and accuracy you'd pay thousands and thousands, maybe even tens of thousands for from a speaker setup, you can drop about $450 on the Shure SE535, which are Shure's top of the line in-ear monitors, and they're just sublime.
If you want some full-sized "cans" for use at home, I really like Denon's high end headphones. I really love the "old" AH-D5000. And while I haven't heard them myself yet, the new AH-D7100 are reportedly magnificent. You're getting into some pretty expensive headphones with these, but again, $1000 is a small budget for a speaker setup. For headphones though around $1000 gets you flagship quality sound. So it might seem crazy to spend that much on headphones, but not if you think of them as just being very specialized speakers!
Maybe you just want surround speakers right away. Maybe you think you don't care about room acoustics or getting your house and car first. Maybe you don't want to live with a merely "great" and very versatile "entry level" surround speaker system like the one I put together and recommended here:
$2500 Complete Entry Level Sytem (Audio AND Video)
until you've got your house and car and you can let the room you've selected as your theater dictate what gear is going to work best for you. That's ok. We've all done it
But if you want to spend your money as wisely as possible. If you want to get every penny's worth. If you want to spend as little as possible in the long run. Get some great headphones. Get a MixAmp. And/or get a great entry level system like my $2500 suggestion. And then wait. Work hard. Make a buck wherever you can. Save it all up. Don't spend a cent more on home theater gear. Plan, plan, plan. Find the house you want with the room for your theater that you want. Buy it. Build the theater room. And then fill it with the gear that's appropriate for that room. The specific products are all going to be new by then. So there's not a lot of point in worrying about it right now. But you'll be happy in the knowledge that you didn't waste a cent along the way, you're streets ahead of your lazy friends, and you were enjoying great sound from your headphones and/or entry level system the whole time, so you didn't even "miss out" while you were working hard and saving up. And now it's time to treat yourself for all that patience and all that hard work. And it'll feel all that much sweeter because you'll truly know that you've earned it
Hope that helps!