As far as senders, from what I've seen AWS SES is still probably the basic go-to for the HN type, pay as you go pricing looks to be quite good in this context and most of us are familiar with navigating AWS. Without any major experience, it seems to work in my light kicking of the tires so far. When I tried Postmark more heavily like a year and a half ago it seemed truly excellent for a more full fat flat per month service, and that's what I'd planned to move to already following the legacy GSuite sunsetting. Unfortunately bad timing for me, they finally decided it was time to move on and sold last year to a marketing company [0], and since then there have been significant price increases, elimination of non-subs, and a few concerning events. I think they were the last of a big grouping of '09/10 email startups to do the acqui-exit. Doesn't mean they won't still work and aren't mostly still fine, but something of note. Mailgun, Sendgrid and so on are all farther along the post-acquisition curve there. Last month there was a new one announced on HN called Resend [1] which is more development oriented but still of interest.
On pricing/ROI: most of the paid tiers for monthly plans seem to start $15-20/month now though with free tiers to experiment with first. I think self-hosting tends to pay for itself best if you fall into certain now neglected niches and have existing infra, or else are willing to pay some premium ideologically. Most email services now tend to squish a bunch of the actual underlying stuff into a specific payment model: mailbox (email address) is 1:1 with a person, and also covers storage, while people don't really think about sending numbers. Whereas underlying storage is actually dirt cheap particularly in the context of email, mailboxes are effectively free, but sending emails costs. So for example I have a bunch of domains and lots of email accounts at them, I was always in the habit of making heavy use of separate mailboxes for basic utility usage like a server sending a status alert (and that also means the server email address can be restricted and not have credentials fro my personal or work email etc). Low volume, tons of mailboxes, occasional big messages with logs and such is an absolutely awful fit for most mail services and getting worse. I also have reasonably solid self-hosting infrastructure already that I've amortized for other things, so at this point essentially adding another VM is quite efficient. For someone who falls into the general bucket, just going somewhwre like Fastmail or even GSuite or the like would almost certainly make more sense. $15/month would buy 3 of Fastmail's standard "users" (ie, mailboxes/different addresses). But I have way more than that, lots of which only send a handful of emails. Doing that with Fastmail/ProtonMail/Gmail/etc type pricing would be hundreds of dollars including $5/month accounts that receive nothing and might not send more than a handful of emails per year.
Anyway, that's my thinking and what I've been experimenting with so far. But ultimately part of the point/value of it all is that on the "difficulty of change" scale, moving to a new email address entirely is the worst though cheapest, owning your own domain and being able to point at a new email provider then is vastly easier but costs domain/year (this mid level is probably best for most people), and having merely to change relays on a server costs the most but is the most transparent. So trying to get out of the habit of thinking of these things as needing to be long term relationships. If a relay service isn't working for me with self-host or someone offers better I'll just move. I'll probably keep one or two addresses traditional too as fallbacks.
On pricing/ROI: most of the paid tiers for monthly plans seem to start $15-20/month now though with free tiers to experiment with first. I think self-hosting tends to pay for itself best if you fall into certain now neglected niches and have existing infra, or else are willing to pay some premium ideologically. Most email services now tend to squish a bunch of the actual underlying stuff into a specific payment model: mailbox (email address) is 1:1 with a person, and also covers storage, while people don't really think about sending numbers. Whereas underlying storage is actually dirt cheap particularly in the context of email, mailboxes are effectively free, but sending emails costs. So for example I have a bunch of domains and lots of email accounts at them, I was always in the habit of making heavy use of separate mailboxes for basic utility usage like a server sending a status alert (and that also means the server email address can be restricted and not have credentials fro my personal or work email etc). Low volume, tons of mailboxes, occasional big messages with logs and such is an absolutely awful fit for most mail services and getting worse. I also have reasonably solid self-hosting infrastructure already that I've amortized for other things, so at this point essentially adding another VM is quite efficient. For someone who falls into the general bucket, just going somewhwre like Fastmail or even GSuite or the like would almost certainly make more sense. $15/month would buy 3 of Fastmail's standard "users" (ie, mailboxes/different addresses). But I have way more than that, lots of which only send a handful of emails. Doing that with Fastmail/ProtonMail/Gmail/etc type pricing would be hundreds of dollars including $5/month accounts that receive nothing and might not send more than a handful of emails per year.
Anyway, that's my thinking and what I've been experimenting with so far. But ultimately part of the point/value of it all is that on the "difficulty of change" scale, moving to a new email address entirely is the worst though cheapest, owning your own domain and being able to point at a new email provider then is vastly easier but costs domain/year (this mid level is probably best for most people), and having merely to change relays on a server costs the most but is the most transparent. So trying to get out of the habit of thinking of these things as needing to be long term relationships. If a relay service isn't working for me with self-host or someone offers better I'll just move. I'll probably keep one or two addresses traditional too as fallbacks.
----
0: https://news.ycombinator.com/item?id=31247296
1: https://news.ycombinator.com/item?id=36309120