Not being able to share this font legitimately with my printer and web designer is ridiculous.

You should be able to send a font to a printer, but not a web designer. A web designer is a professional designer just as you are and needs to buy his own font licenses to use them in his work.

I think he means an outsourced printer(person) as opposed to a printer (hardware) in his office. I believe LHF used to have some way of preventing copies being made of their fonts and thus making it difficult to send out for a specific job. Best to contact LHF about your issue for printing. I believe the web designer would likely need to purchase the font as well. If you're just making images for the web as opposed to any kind of active web type you could create the images to your web designers specs and send those.

Asylum » Sketched, Scratched, Scribbled
Chesham Sans » Abadi, Sweet Sans