The most important resource I have is my energy, and being able to trade X dollars (where X is any number less than a hundred) for even trivial amounts of energy is an absolute no-brainer.
When I launched Buttondown, AWS Simple Email Service was notoriously low-quality and Postmark did not support broadcast emails. Mailgun was the choice I went with, and there are still many customers using Mailgun's rails who have custom domain records set up that I don't have the heart (or incentive) to migrate.
I like having redundancy — if one provider were to go down or drastically change rates it would be trivial for me to migrate — but if I were starting Buttondown from scratch I would likely just have everything run through Postmark.
Some specific choices I made to roll my own: