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Double Bass Gradual replacement

I've finally hit on the idea that my (cheapish plywood) bass might sound better if I got new strings (probably Obligatos) to replace the ones that probably weren't new when I got her ten years ago.

As a starving student, I was thinking of upgrading one at a time, as I have the spare cash, but this raises the question of where to start... I'd be tempted to get a D or an A to get nice mid range for playing jazz and folk, but would this leave me with issues for orchestral playing if the tone varies a lot over the range of the instrument? Would it be better to start with a G?

Sorry if this is a slightly obsessive question, but I'd rather not spend a couple of months getting confused by a comical sounding bass.
 
Hold out for a full set. Yeah, I remember the starving days, too, when I wondered how the hell I'd possibly pay for a Golden Spiral D&G. But in the long run, you'll be better off -- you'll have an all-new set, equal amount of time on each string, and you'll save money if you intend to buy online; it'll probably cost you around $5 per string to ship, so you're looking at $20 just to get the singles to you over time.