New modem or router first?
PROBABLY around 70 or so
Both your router and your modem aren't great, but I've had that router and had tons of problems with it, so I'd recommend getting rid of that first.
The router I most recommend at that price point is the ASUS n600, it's solid, easy to use, and feature-full. The only issues are that it doesn't have external antennas, so range won't be quite as good as one with external antennas, and you can't replace the antenna to get better coverage. But this probably won't be a problem for most people. The other concern is that it does not support the new wireless AC standard, which there aren't many devices for right now, but there will be in the future. So if you get some of those devices, and you want to use the high bandwidth... you see the issue.
The price for them fluctuates a lot since they're a bit older. They're like $85 dollars on amazon, but my local frys electronics consistently has them for around 50 bucks. You can also get them for as low as 25 on ebay, if you want to go that route.
My recommendation for modems is always whatever Motorola Surfboard fits into your budget. I have the SB6120 (on the same internet package as you), and I'm quite happy with it. It can be had for around $20-30 on ebay. The new model, the SB6121, is about $60, and I assume it's good.
So actually, if you're comfortable with buying your stuff used, you could get both of them for under $70, and then it would be more okay to upgrade your router sooner, since you wouldn't have spent as much money.

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