According to this (
https://www.rei.com/product/797349/s...-s30-bike-2010) the Original poster has an Al-frame, carbon-forked 9-speed with 50-34 chain rings and a 12-26 cassette. His rear derailleur (2010-vinatge 105) can certainly handle 30 teeth, but if he wanted he could go long-cage Sora and 11-34 or whatever .... Much cheaper than buying a new bike, and much smarter.
No reason for him (her, if applicable) to drop a grand on a bike which isn't as good as what he has. For a grand he would probably be getting Claris and heavy everything. he is way ahead of the game right now, with a 20-lb bike.
I am old, fat, and slow, with asthma and a bad heart, and I hardly ride lately, I can get up almost an 4-5% hill with 34x26 ..... I am sure the OP just needs legs, lungs, better cardio, and some technique and he will be fine. if he really cannot handle the hills .... i have no idea how long, tall, or frequent they are---he will still be way ahead just swapping the cassette and maybe RD.
If he repairs bikes though .... he can always be on the lookout for a garage queen. If he fixes bikes he will know one if he sees it. So he has the best of all possible worlds, a decent bike to ride and the cash to buy a very good used bike, and the capacity to recognize a very good used bike .... he wins on all fronts.