In the self managed world you need to do your own updates. That mean staying on top of releases (being notified of them) and doing upgrades when appropriate. You'll have to schedule time for that and have someone that can do that.

Or, is that something the hosting is still willing to do for you?

Why not a vps (virtual private server)? You get all the chewy goodness of a private server (mostly) but there's someone still there to manage it for you. Unless you're getting mad hits and you really really need your own box, vps might be the way to go.

Well, I understand that I'd need to stay on top of security updates, and backups, but is there anything more to it? One of the main things i'm looking for is SSH access to the server. On my virtual hosting, my host won't allow this, and I'm wanting to use rsync for backups. Maybe there is a different way of going about it. Also, I'm worried what if I mess something up, I have the backups, but I don't want to be down for an indeterminable amount of time. What are your thoughts?

What kind of backups are you talking? Database, php scripts, audio files, all of the above?

Because if it's just scripts + db, then you could probably write a simple cron script to get your backups done on time. I had a script somewhere that would back everything up and then email it to me, but I'd have to search for it.

But both slicehost and linode allow for ssh access. They've got reasonable prices as well. Once my website starts to get mad hits, then I'll switch over to a vps since I can't afford colocation.

I moved my personal domain and church domain to a VPS recently and so far it is not too much work. I went with Future Hosting and they have been really good about answering any questions that I have had or fixing things that I was not ready to do myself. They run specials every week. I am paying $32 a month for a cpanel VPS with 768 Meg of RAM and 40 Gig Hard Drive space. It is a managed VPS so they will help keep OS and CPANEL items up to date.

If you're running a VPS and you're not getting SSH access, then you're getting ripped off, unless you're speaking of shared hosting, which frequently does not come with SSH access.

I'd second the VPS method, unless you really want to learn about server management.

When you self-manage, you trade time for money. It will take more of your time to manage the system, but in return you're paying less than you would for comparable resources the host manages. Your biggest question will often be "what's my time worth?"

I recommend you peruse "Time Management for System Administrators" by Limoncelli. It's an O'Reilly book, written from the point of view of a sysadmin with tips and tricks for efficiently managing a system. Take a peek first, because you may not be fully aware of everything you'll need to do and keep that peek in mind. It can help you make a knowledgeable decision.