When promoting affiliate offers, just make sure you are fully aware of all the terms and conditions attached to your affiliate program. Some programs can be strict about how they allow you to promote their products. For example, some may limit you to banner ads and links only, while others will allow you to use paid advertising, but won't allow email marketing. 
You may also want to check out 9 Best Content Marketing Training, Courses and Certifications; Best Instagram Marketing Training and Courses and Best Courses on Coursera. In addition to that, you will find 7 Best EMail Marketing Courses really useful and the 8 Best Shopify Marketing Courses will help Increase Sales and Profits. All the training programs mentioned above are so affordable, they are nearly free affiliate marketing training.
Regarding “convincing someone to buy your product is not that easy”, I do agree with you, but at the same time, I remember all those products I’ve bought online. I did not search on Google for those products neither I went to the company websites to get information and buy. They were affiliate people and their blogs that inspired to buy them. PrettyLink Pro, SEO Pressor was recommended by Kimberley, I bought Profits Theme, WP Zon builder because Alex Whaley recommended. Similarly I bought CommentLuv Premium because Ileane, Kavita, Steve and many others were talking good about it.
Same here, this post kind of fell from the sky at such a great time. Been building a great community of readers over the years but reached a point where I’m losing money maintaining the site and newsletter. As you said, the ads don’t bring much -ironically I use Adblocks too but affiliate marketing always seemed like a weird and opaque subject. I’ve read many of Chris Guillebeau’s books in the last few months (this is how I discovered your site actually!) and I didn’t realize he had affiliate links for instance. Your post opened up a new window of possibility for me. Still need to process everything and do the work behind but a big thank you to you Sean!
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