In general I would agree to your advice of taking small steps, but with the concrete examples, my former self would think "but then everyone remembers me as the creepy guy, who just comes and looks at everyone. I could not go to step 2 then"
Another thing that can be much easier while traveling if you have anxiety is dating. Like you said, there's the comfort in knowing that you'll never see any people there again if you so choose. But if there's also a language barrier, it removes any expectations of witty banter and flirtation that usually relies on familiarity with your local culture and social norms. And there's less pressure to be interesting -- just being a foreigner will often make you interesting to locals without even trying, at least a first.
