I love self-hosting. Both at home and in the context of running a VPS or dedicated machine with your “own” software. I hate when things break or you forget about a gotcha.
The ability to customize and control and relatively own your data is great. Spending your night resolving an issue or having to think through a design is both a great experience and constant source of frustration to me.
The ease of paying someone to deal with all of this is great. The tradeoff of loss of control and options stinks. Yet those of us that opt for this path continue to do so.
At least I learn things along the way.