Any time I want to add money to my Tip Jar an automated comment will be created that I will then self-upvote.

The self-upvote approach for funding the tip jar will unfortunately be inefficient after HF21 due to the contingent linear reward curve. You'll only receive around 50% of your full vote value (unless your vote is more than something like $6.40!). You would be better off upvoting the post.

What happens if someone starts flagging you because you're quote, "Only self-upvoting"? Well, in that case you can sell your vote and acquire the liquid SBD/Steem instantly and add it to the Tip Jar that way.

I think this style of approach will work better. Acquire the maximum you can for your votes, whether through vote-selling, community aggregation, delegation or investment in a curation-bot fund. Then use the liquid amount received to tip users directly.

I had broadly the same idea as a means for getting around the contingent linear reward curve issues for small accounts looking to upvote comments (and by small I mean everyone who isn't a whale). I think we'll see a lot of this form of innovation after HF21 to get around the market inefficiency being introduced.