How much will you make? I think my best month with Google AdSense was almost $5,000 over the last ten years. That amazing month blew my mind since it was actually near the beginning of my blogging journey. When you go from making zero to $5,000 in a month, that will rock your world. For me, it also got me even more excited because I knew there were other ways to monetize.
Will my target audience realistically buy this now, or at a different time? Be sensitive to sales cycles and seasons. Maybe you should avoid holidays (when people are away from their computers, like July 4 in the U.S.) or maybe you should target holidays (like the day after Thanksgiving), but know the difference. Again, know your audience. Plan your content accordingly.
If you have pop-ups and optins on every page, I would have to think that it would be a lot harder to convince someone to link to it. Especially since the pages where you have your optins (and probably receive the most traffic) are probably the same pages that you have your best content on as well that you'd be hoping to pitch in your outreach campaign.