yes. i will give you my personal experience from 3 years ago and last month.
3 years ago:
gmail/outlook was an ass. They marked all emails as spam. I had to call recipients to check spam and mark as not spam. this was on-off for the first few months. then things went good on their own.
They would mark spam initially all emails, then emails with attachments then once marked as not spam, things got better.
today i have 0 issues in outgoing email. funnily, i have a website that sends me emails and there is some unknown problem on "receiving emails". just one website so haven't had much look into it.
last month:
followed the same setup and gmail/outlook made no complaints. this was surprising to me as i deliberately sent attachments but nothing.
one thing to note. i once send 15-20 mails in bulk (not cc/bcc but separate) at once and that triggered some spam response. marked as not spam fixed it though on recipient side.
both times i used mailinabox and a cheap vps from lowendbox deals. racknerd or something on offer.
takes 1 hour almost from domain/vps purchase to full setup and sending emails.
backup on backblaze b2.
takes 5 minutes every 6 odd months to update the software but that's about it.