Per the File::Tail documentation:

select is intended to enable the programmer to simoultaneously wait for input on normal filehandles and File::Tail filehandles. Of course, you may use it to simply read from more than one File::Tail filehandle at a time.

Your answer makes sense because it doesn't seem to work, but I'd say that documentation is quite misleading. I did find this bug that may be related, but it hasn't been updated in 7 years, so I'm guessing development on this module stopped a long time ago, in a galaxy far, far away...

So for now, I believe the fork/thread methods suggested by aitap and zentara are my next learning adventure...