If you have access to a shop that rents lenses, that will be money well spent. Guaranteed!
The 17-55mm is a wide angle lens that is mostly used for landscapes. The close range distortion makes for some interesting shots in other genres, but it's not something most would use for traditional portraiture or lifestyle photography. The optimal focal range for portraiture is 50-80mm, and using a wide angle lens for portraits will distort facial features unless you can get your distance from subject exactly right.
You're at a crossroads. I see what you're wanting to do, and most of us have been there too. Crossing the threshold from hobbyist to enthusiast is an expensive one. We all want an arsenal full of top end gear, but few can afford it. You want to get the most bang for your buck, and that's understandable. There are two schools of thought on this:
1) You have a $1000 budget, so spread it out. Diversify. Get decent lenses, but get as many as you can afford. Buy used and shop for those rare bargain basement deals.
2) Take that same $1000 and invest it in the biggest, baddest single lens you can afford that meets your needs. If you're wanting to focus on portraits, there is some nice kit to be had out there in this price range. But also realize that portraiture is just as much about lighting as it is anything else, so there's another investment down the road to get the most out of this strategy.