You can do that with the one button, sure, just set the initial amount at 199 for 1 month, then the regular amount at 99 every 1 month. The affected attributes for the shortcode would look like these:
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ta="199.00" tp="1" tt="M" ra="99.00" rp="1" rt="M" rr="1" rrt="" rra="1"
WP Admin -> s2Member -> PayPal Buttons -> Shortcode Attributes (Explained)Of course, you can generate that with the button generator, but reading the definitions for those attributes will help you understand what's going on with the shortcode and even edit it manually if you feel like it.
I hope that helps.