It's a hard choice, to be honest. You've listed most of the pros and cons, I'll add a few. Monolights are a lot more powerful - can use with bigger modifiers, can overpower the sun for outdoor use (you can do that with flashes, but you'll likely have to gang 2-4 together per modifier).

While you're correct that a 7D can be a wireless master, I'd recommend going with RF triggers. The optical receiver can be seen with my Lastolite soft boxes (you rotate the flash head 90° to stick it in the box, leaving the base out and not pointing at the side of the softbox), but that requires careful positioning of the flash/softbox, and precludes some positioning (such as lighting a background from behind a subject). With RF triggers, you don't need to think about it, which is a big advantage especially when setup speed is important (such as at a friend's house while they're standing around waiting for you to get set up).

Hopefully, Sean will weigh in with ideas and his vast experience!

Personally, I have a blended setup of Speedlites and a monolight, with PocketWizards and the Canon -RT system, and it works well for my needs. I really like the Paul C. Buff monolights (particularly the Einstein) and their modifiers are a great value...but I'm not sure how easy they'd be for you to get (made in the US and only sold direct to US and Canadian customers, so you'd have to pay by wire transfer and use a freight forwarder).

I will say that the Canon -RT system is really robust and easy to use. I've got an ST-E3-RT and three 600EX-RT flashes, they're pretty powerful and very reliable. I use them with a pair of Lastolite 24" Ezyboxes and a Lastolite 12x48" Hotrod Stripbox. That setup is great for portraits of 1-2 people. The Lastolite boxes are fast to set up (especially the Ezyboxes, which just pop open and you press the diffusers onto the velcro edges - I wish the strip box was like that, but it's the wrong shape for a foldable box).

I also have PocketWizard triggers - a MiniTT1 for on-camera, a pair of FlexTT5s for Speedlites, and a PowerMC2 for the Einstein monolight. They also work very well for me. I use the AC3 zone controller on the MiniTT1, and it's excellent for quickly adjusting the power levels of the different flashes. Basically, I choose the monolight and a pair of flashes, in which case I use the PW triggers, or just Speedlites in which case I use the ST-E3 as a master.

My lighting support is all Manfrotto - IMO, they offer very good quality and value. I've got a pair of 12' stands (1004BAC) and a pair of 7' stands (1051BAC), and I also have the 1314B background support, and that includes a pair of 8' stands (1052BAC). The stands fold flat and clip together for easy storage and transport. I frequently use the 7' stands to support the background (the 7' stands have a 2' diameter footprint, vs the 3' diameter of the other stands). The 7' stands do fine with a speedlite + modifier indoors, outdoors the bigger base of the 8' stand is needed for that (and sandbags on the base). The 12' stands hold a monolight with softbox, and is also good for extra height outdoors. I also have a boom (024B) which is great for getting a light over the subject for a hair/rim light or to light the background. That boom, when used on a 12' stand, will support a monolight and stripbox. If you go with a Speedlite only setup, you might consider at least one Manfrotto 420B combo stand - it's a 12' stand that converts to a boom with sufficient strength for a speedlite and a softbox.

Good luck!