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Where cataory should I hire fiver? it is about SEO, worldpress, and url?

I have site made of html (dream weaver) with over 300 page. Currently, I have around 170-220 Visitors a day. I sales tour in Thailand. I would like to move this site to wordpress. I notice that wordpress will generate url automatic and it can not be something with .html at the end . My ulr of news page in worldpress will have completely new url. It will completely effect to SEO. I need help for guideline how to fixed it step by step. Where should I post to ask from expert ?

For example original url is . when move to worldpress. It will be

Can help with that