Question, I have thousands of urls (http://domain.com/category/1.php) and I need to 301 redirect them to my new domain url structure http://domain.com/category/1231/good-url structure.aspx. If I 301 redirect my .php page to .aspx page that redirects to another .aspx page, is that a bad thing.
I don't think that's a bad thing. Just make sure that your redirect from one .aspx page to another .aspx page is also a 301 and not a 302
This must be a common scenario. Company A merges with Company B. Company B wants to reduce site content from 200 existing pages to 50 new pages. For example, the current product section has 5 pages that will be consolidated and 301 redirected into one page. What is your opinion on 301 redirecting multiple ULS (with different content) to a single page?