I'm about to work on a retail product website that has been around for about 10 years. The website ranks nicely in Google search results. The website has evolved a lot over the years so it's no surprise their .htaccess file is full of 301 redirects and rewriterules. There are so many rules it's an eye sore. Sometimes there are three different legacy urls that 301 redirect to the same destination. I'm concerned this file will be a nightmare to maintain down the road.
Does a web developer ever reach a point where he's willing to remove old redirect and rewrite rules for easier maintenance at the cost of SEO? Or does Google have a copy of the website's 301 redirects, in which case, I can remove them from my .htaccess file without any SEO penalty?
How does a developer deal with a messy/lengthy .htaccess file?