Sending bulk emails with attachments.

Try using salesmate. They usually cater to small businesses so their packages are relatively cheap. User-friendly, and are generally less buggy than more commercialized options like buzzstream, in my experience.
 
I've just had a good look at salesmate and it still seems to be too marketing oriented for me. In the meantime I've switched to Mailerlite which is free and is useable although doesn't allow for attachments.
I can't think of any other small software, have you tried Klaviyo? It's very marketing-oriented but I've heard nothing but praises from people I know who use it. They're one of the few options out there that have a free version too. I worked once with an agency called CodeCrew which markets themselves as "Klaviyo experts", and I knew then that Klaviyo has its own ecosystem of agencies and individuals for the sole purpose of mastering Klaviyo itself.
 
You could host your attachment on Google Drive for free and then send the link to up to 500 people via outlook. Just make sure you add them to BCC instead of To or CC.
 
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