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Will it hurt me if i redirect a few hundred old pages to my home page?

I currently have a mess on my hands with many 404's showing up after moving my site to a new ecommerce server. We have been at the new server for 2 years but still have 337 404s showing up in google webmaster tools. I don't think it would affect users as very few people woudl find those old links but I don't want to mess with google.

Also, how much are those 404s hurting my rank?

Do I need to have links to all of these landing pages? I'd rather not if I don't have to

I love the keyword tool for giving me direction and helping to prioritize. My question:

Once I have the prioritized keywords, do you recommend having a page for each of the top keywords, using the keyword as the page name? Or is it better to sprinkle the keywords into existing pages?

Thank you.

Thank you

I have not already 301'd the site to https. But either url works since I turned on the ssl at my host.

I will check into the Cloudflare.