Kobo compares favorably to Kindle. Really they just lack something like "Send to Kindle" but they make up for it with other things. Some models support Dropbox syncing, they support getting books from the library via. Overdrive right on the device and they have a lot more customization with regards to what you can do with fonts, spacing etc. out of the box. And you can even get pen input for note taking on the bigger ones if you want.

I'd just pick the model that most appeals to you with exception of the base model. I think the extra $30 to get a 300PPI screen is worth it.

I can't compare directly with Kindle, as the last one I used was a couple of years ago.

But the features that directly appealed to me are stylus support for two of the latest models: Elipsa and Sage.

It has support for Overdrive as far as I know (though not in all countries). It has support for dropbox. It supports more formats, which makes it a favourite for sideloaded manga/comics reading.

It's easy to root and run your own code on it, there's a pretty healthy community of modders out there. Under the hood is just a linux machine.

Additionally, the larger form factor is really nice, as my eyes start to age.