Suggestions for a SR4a Decker Concept Options

[DnDer]

My GM is going to run a side game for the next few months for just two people, so we can learn and focus down the SR4a Matrix rules, and also because he wants to go to Montreal, since the book was published (which he claims is a great place to be, if you're tech-oriented in post-Crash 2.0).

Here was my pitch: Pre-crash decker, grizzled veteran of the Matrix, long since settled into Montreal and adapting nicely to the wireless world. He's been making enough of a living for himself cooking chips and doing upgrades for runners' e-gear, and hasn't been on an actual run himself, in ages. Now, <plot-driven impetus> is forcing him to dive back into the life of a runner in the post-Crash world.

Simple (and cliche, I know) enough to work with... But I want to grab onto some of the good old fashioned cowboy spirit missing in the wireless world. Not necessarily "get off my lawn" old, but he's going to have some years under his belt, and the second player has decided on a technomancer archetype. We'll be using standard karmagen instead of BP.

Is there any gear or PQ/NQ I should keep my eyes open for? I know I'll have to invest some of that in kits and workshop to fit my background, but I don't think it's an unreasonable cost.

Being that he's no longer bleeding-edge SOTA, I was thinking of NOT having the best link out of the books, and forcing myself to work with something second-tier, or cooked according to the rules for upgrading. On an average run, can a hacker accomplish anything if he doesn't have the bleeding edge equipment and the entire host of programs at 5s and 6s?

Or is this, "All good and well for a novel, but just really burn the concept and go put together something out of the box with proper gear, instead of being a moron about less-than-optimal options?"