Your errors are because you only used the hyphen indicating switch on the first attempt, but not in any of the others, making it think you're using filename wwc as your input, invalid attempt to use a #channel as output, and searching for text string @filter followed by *land*. Multiple switches are combined as 1 parameter, but it must begin with the hyphen.
Some switches require the presence of an additional parameter. For example, the n-n2 parameter should only be used when using the -r switch, and the c and s parameters should only be used alongside the -t switch.
There's several websites that try to teach regex, once you're ready to create a search, you can use regex101.com to try "what if" scenarios to see whether you're matching everything you should and aren't matching things you shouldn't. While learning what you can and can't do in a regex search, you should try getting a search/pattern working there before using it in mIRC. There are some cases where commas and other special characters are not handled as you might not expect, so it's probably a good idea to put the search string in %pattern then use %pattern as your regex string.
var %pattern (land|controller)
//filter -wwg #channel @window %pattern
Returns lines containing either string, but also finds them when they're part of another word, such as bland or grand.
var %pattern \b(land|controller)\b
This forces the match to be a whole word. However there are no switches being used, and regex defaults to being case-sensitive, so if you want to match either Land or land, it needs to be case-insensitive
var %pattern /\b(land|controller)\b/i
1. You can't use multiple windows as your input. You'll need to hit them in series.
2. If you want to use the timestamp for sorting, you might need to alter the format to include the seconds, and possibly the date, to prevent 23:00 sorted after 07:00. You're wanting to sort by the 1st token of the line, and your tokens are split by the space character 32, so "c s" are "1 32".
3. To update at intervals, you can use /timer. I assume you would want to avoid repeating things that displayed the prior time. You can save the prior output to another window first, then can examine the current output for matches against the old-match window. Otherwise you would "/clear #channel" after getting matches so they can't be found again.