Ok, so currently I own the following:

Canon t2i
Canon 18-135mm (my walkaround lens)
50mm 1.8 (for products/portrait)

I'm looking at purchasing either the
70-300mm (I can get it for 355)
or the 100mm 2.8 macro non-L (I can get for 360)

Eventually I want to shoot some sports for fun. I also want to endeavor into macro. I also eventually want to upgrade bodies to a 5dm2 and pro lenses.

That being said, what do you guys think?

telephotos are nice and the 100mm would be cool, but i guess it depends on what you like shooting.. imo you could use a wide angle lens because people more often take broad pictures rather than super closeups.. unless closeups are your thing

Actually landscape/urban architecture is one of my fav things to shoot, but I can't afford the 10-22mm or the tokina 11-16 right now.

you can get a sigma 10-20 on eebay for pretty cheap like 300-400

Honestly, I'd rather not get a crappy wide angle. I'd rather wait and pay for quality on that one.