Question for the sysadmins in the house: Server, Hosting, and CDN advice and experiences

Although this isn't strictly a Drupal question, the Drupal Pgh meetings seem to have a sysadmin contingent so I hope this falls on knowledgeable ears. With more clients asking me to host and maintain the sites I build for them I think it's time to move on from cheap shared hosting options to something more robust. I don't have very much experience with servers aside from the standard interactions front and rear end devs normally have, so I'm looking for some advice/experiences.

My use case slash requirements slash want list:

• Will be hosting 5-15 Drupal sites, all separate, non-multi site installs (some projects require less stable dev modules, and I prefer to keep most sites self contained for ease of migration if the client requests it in the future). A host with services optimized for php/mySQL sites would be preferred.
• Need higher than standard shared hosting memory limits (128mb ram min, 256mb or more would be ideal) for imagemagick/gd transforms on print quality images.
• Need to be able to point 20-to-unlimited domains to the same hosting account (not nec. all sites, or cms sites of course).
• Looking for around 2-5gb storage, 20gb+ bandwidth a month (those aren't current numbers, just planing for the future).
• edit:SSH is a must.
• Traffic is on the lighter, small business side, but would like burst to ensure uptime during possible high load situations (featured in trade publication, blog linked on high traffic site, etc).
• Good uptime is (obv.) important, but as of now these are business sites not apps. 99.9% is good, anything above is icing.
• For server location, most serious customers in US, so that takes precedence.
• A good control panel would be preferable, as would automated backups, redundancy, or cloud storage.
• Clients will be paying for space but will not have any interaction with server config themselves.
• Would like a company that offers the next tier or two up from what I end up purchasing. If any sites in the future grow to have greater needs I'd like to be able to transfer them to a new plan in house, as opposed to finding service elsewhere and increasing the accounts I have to deal with.

So I am thinking a semi-dedicated shared or a VPS on a cluster or small cloud service is what I will be looking for here. I'm already an over-generalist so I'm not relishing adding server management to my list of partial skills -- something that doesn't require full attention maintenance is strongly preferred, a managed solution I guess if I need it. I assume server setup and management is not an amateurs game, and I don't want to pay for quality then leaving gaping security holes open or constantly crash the server myself. As for price, I'm shooting for something near the $20-35 a month range, and I'd rather have lower numbers in the stats and better support and reliability than vice versa. Feel free to tell me if I am living in a magical unicorn fantasy land.

Some companies I'm looking at are ASO, MediaLayer, Cartika, Linode, and MDD. Any experiences with these or other companies to take a look at would be appreciated.

Bonus questions tacked on to the end:

I'm also looking to set up a CDN for my static theme files. Any experience with Amazon Cloudfront, Rackspace files, or others? It seems like Cloudfront's directory mirroring could be used easily with Drupal for some dynamic content as well. Any experience with Cloudfront's per-request plus per kb transfered pricing?

I'm also toying with the idea of going with a host that uses Litespeed webserver instead of Apache, or maybe setting up something comparable it if I go the VPN route. Any experiences, caveats, love-hate relationships, etc, would be appreciated.