Find an Envelope printer

I was lucky enough to have a printer that does envelopes well. My laser printer allows me to load up to 95 envelopes in the trays ( another 80 on the 3rd tray) and just do a mail merge

It is an OKI B6300. it has been discontinued but you could find it at a discount on amazon or ebay.

Laser might not be the way to go:

Laser printers with a straight path that can handle envelopes are rare and expesive. Your best bet if you want to print around 500 envelopes is to buy a good ink jet printer that states it will handle at least 10 envelopes at a time.

Remember, “paper handling is everything” you do not want to be stuck applying 500 stamps 500 labels 500 return addresses.