If you send an normal email to a client and then place a special email in the mail (you get from Highrise) out in BCC the email will be put into the right place in the system, on this way you can use you own email program. Highrise find the "to field email" and secure the mail stored under the right account in your CRM. Perhaps this is a good idea?
You actually get 5 different mails you can use in BCC one of them also book a reminder in the system 1 week after, another 2 weeks after like that. On this way you can also use your own email system to mass email more than the 30 we have her today.