Do any of your emails actually make it into an inbox though? I did this for a server and I couldn't even get it to land in spam on gmail.

Yes but you may need the IPs to warm up and build some reputation, depending where you setup your server the IPs may be burned. Check logs and reputation with some of the postmaster tools the major providers offer and with the services that allow looking up an IP. senderscore used to be convenient to use now it displays a stupid contact form when you try to check an IP, there are others.

To be honest I haven't done the setup for sending a handful of emails but IPs sending hundreds/thousands per day it's fine as long as you don't start spamming people and get flagged.

Yes they do. I wouldn't try it from a residential IP but as long as you run a blacklist check on the IP before you start, and configure DNS correctly, it's generally fine.