It should be very clear that ads are ads, not questions
"Tricking" users into reading the ads by disguising them as questions is probably about as shady as you can get, short of placing unmoderated spam on the site.
- Make the background a different colour. This will more clearly indicate that it is something different. For obvious reasons, the background colour should also be different from the favourited tags' background colour
- Respect ignored tags - If I've ignored python, why should I see ads tagged with python? That does your ad partners a disservice too, as its extremely unlikely I'll be interested in anything to do with Python
- By the same token, ad partners should have the same "5 tag" retrictionrestriction as questions. Otherwise, ads will just end up being tagged with the top 40 tags every time.
- Give 10k+ users tool pages to review ads placed against tags. Ad moderation should be proactive, not reactive. Put the power in the community's hands to apply some level of moderation on the sorts of ads that appear on certain tags.
These changes would be a massive improvement, though I will say I still don't like this idea at all. Build a merch shop and I'll purchase shirts from you instead.