> 2. What's easy to underestimate for _developers_ is that your self hosted setup is most likely harder to get third party support for. If you run software on AWS, you can hire someone familiar with AWS and as long as you're not doing anything too weird, they'll figure it out and modify it in no time.

If you're at an early/smaller stage you're not doing anything too fancy either way. Even self hosted, it will probably be easy enough to understand that you're just deploying a rails instance for example.

It only becomes trickier if you're handling a ton of traffic or apply a ton of optimizations and end up already in a state where a team of sysadmin should be needed while you're doing it alone and ad-hoc. IMHO the important part would be to properly realize when things will get complicated and move on to a proper org or stack before you're stuck.