Jason,
I have a Rebel T2i that I bought several years ago. It had kit lenses. While at the lease one of my lenses was damaged. After careful consideration and with a good deal of input both here and from my nephew who shoots professionally and uses Canon equipment, here is what I did.
As you know, I shoot for my own enjoyment and satisfaction. Consequently no income is derived from my photographic equipment. I chose not to afford "the best". Rather I bought "good" lenses. I also decided to go with Canon "L" lenses rather than 3rd party lenses. I could be mistaken, but should I choose to upgrade from my new lenses, I do believe the resale value of the Canon would be greater than 3rd party lenses.
Here are two that I've purchased in the last 4 months.
The smaller lens is the EF 17-40mm f/4L USM
It has become the lens that stays on my camera and is used typically multiple times daily.
The larger "white" lens is the EF 70-200mm F.4L IS USM lens.
I am absolutely pleased with both lenses.
Two things that I also have incorporated.
I downloaded and am using the Canon Digital Professional Software (it should come with your camera)
I'm now shooting almost exclusively in RAW.
Between the lenses and shooting in RAW, IMHO I've taken a quantum leap in the quality of my photos. It's almost becoming the obsession I have with rifles.
One more thing. I sprung for good quality UV filters, mainly as protection for the lenses.
I plan to buy two more lenses before deer season. I've a deal working on the Canon 100-400 Zoom.
The fourth will be theCanon 100mm f/2.8L Macro USM. I've not yet decided whether to fork out the extra bucks for the IS, which is almost twice the price.
Best,
GWB