Lighttpd

I'm sure there is a better way to do this but I just started with lighttpd this week .

You seem to be new to a lot of things.

Carefully read all of How to get support - please read

Carefully read the error message that lighttpd gives to your configuration.
2023-12-01 11:31:09: (data_config.c.116) Too many captures in regex, use (?:...) instead of (...): ^/docs($|/)|/Downloads($|/)|/Pictures($|/)|/MacPics($|/)|/IpadPicsBackup($|/)|/MacBookPro($|/)|/Backup-tootie($|/)|/openwrts($|/)|/Win10($|/)|/Win11($|/)

Try harder to solve some of your own problems before posting.

mod_rewrite contains a link to those who do not know how to write regular expressions.
https://www.regular-expressions.info/

Regular expressions are used by lighttpd but are independent of lighttpd. Regular expressions were created a long, long time ago.
https://en.wikipedia.org/wiki/Regular_expression

lighttpd 1.4.69 is available from bullseye-backports, so I suggest you upgrade before posting any questions about something else not working that was fixed in the 2 years between releases of lighttpd 1.4.59 and lighttpd 1.4.69.

I changed it to

"^/(docs|Downloads|Pictures|MacPics|IpadPicsBackup|MacBookPro|Backup-tootie|openwrts|Win(10|11))($|/)"

and it works yet I still think there must be a better way

You used regex alternation and now have a working solution. Good.

yet I still think there must be a better way

Read the links provided and think about what they teach.

There are lots of different and better ways to solve different problems.
Carefully read all of How to get support - please read

Since you seem to have missed reading the error message even after being reminded to read the error message:
The error message already provided a better solution: Too many captures in regex, use (?:...) instead of (...)