Not sure if you are currently working with a consultant but we had ours set us up with MyAssistant.  We also switched to ACH vendor payments this year and My Assistant is set up to send a statement to the vendor of what invoices were processed for payment.  I would suggest checking it out because it's pretty neat.  

I believe that the only way to be able to email pay stubs directly from Sage is to use the MyAssistant already mentioned.  We are on 300CRE and just started with the MyAssistant last year.  We currently use it for emailing employee pay stubs and vendor pay statements/lien waivers for those with ACH payments. It seriously saves me a whole afternoon of printing checks, generating and checking lien waivers, stuffing envelopes and sending those out.  Not sure how your company uses 300CRE but we were able to drop a couple of licenses per application that we were not always using in order to offset the cost of adding MyAssistant.  It's definitely worth taking a look at - there are a lot of functions to it beyond the two I mentioned!

Thanks, this is super helpful. Sounds like I need to call and have MyAssistant priced out. We're definitely more on the old fashioned side here, so I'm definitely needing to improve efficiency above all else so hopefully even just the cost of labor to spend an hour stuffing envelopes plus saving on postage will offset it. Thanks!