Doing anything new will require work/pain the first few times. It is just part of the learning process. If that sudden jolt of happiness when you get it working can outweigh the depression caused by hours of trudging through the setup/failures, you’ll constantly be improving. Like all things, give it a fair shot and if it brings you more pain than pleasure, stop doing it.

There are now a lot of people who are making a living from providing self-hosted services to others for small fees. Even if you decide to not self-host, there are multiple ways to get the lion’s share of benefits. Its not a binary choice between Google and self-hosting.