What kind of website do you have ? Is it eCommerce ? If yes, check the revenue and conversion data in analytics. If you are seeing sales in the last 3 months from Bing, then you should optimize for Bing as well.
If you have niche site, check if there are your pages in top 50 Bing search results for keywords you've targeted. Then you can optimize these webpages.
The good thing is that optimization process is almost same in both search engines. On another note, are you using Bing webmaster tool, it is recommended to use this tool to troubleshoot the crawling and indexing of your website in Bing search engine.
I never have honestly, but it definitely won't hurt. I doubt Bing will take up the same share as Google, but it does and will still have users that just may or may not find you through it. So what would it hurt?
The comparison between search results offreed often favor Bing, but people just prefer to use Google as its the 'one' to use - Bing may well be making a come back over time so dont take google for granted
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