Hi Annie
I'm surprised there hasn't been lots of answers to your question.
Check-out this video here on SEOmoz entitled "Whiteboard Interview - Google's Matt Cutts on Redirects, Trust + More" featuring Matt Cutts being asked some questions by Rand. It opens with a partial answer to your first question:
"These days we use it a little less" (2 years ago) ~ basically means that in locations such as the US, most of Europe, Japan... & so on, where Bandwidth is rarely an issue anymore, 'If-Modified-Since' isn't taken notice of, it's not worth including anymore.
In say developing countries where bandwidth is sometimes still on the low side, it may still be used, hence why a sweeping 'it doesn't matter anymore' statement wasn't given.
**Your second question: **
- Content, fresh unique value-adding content that is, that's engaging and shareable, is always a positive aspect to work on, which in turn can lead to some awesome new links. This encourages the bots to visit more regularly.
- Ensuring that your site doesn't have any technical issues (say causing significant downtime).
- Ensuring that Robots.txt isn't wrongly disallowing any pages from being crawled.
- Keeping an eye on Google Webmaster Tools (& Bing Webmaster Tools) for any messages or errors.
- You can alter the crawl rate in GWT, though is usually best to leave it on the default auto setting.
Hope that helps,
Simon