A VPN, even in another country is not really helping for high anonymity.
Depending on the country a chained proxy like you described it is of course helping a lot, but in all those scenarios it depends on the interest of a damaged company or the interest of the authorities to track you back. If they really want you they will catch you in such a case.
I'll try to answer your questions, I see you are already pretty experienced with Tor:
DNS leaking is solved in the Howto: http://www.cloakfish.com/?tab=howto#howto_firefox-dns-anonymity
In the Cloakfish options you can select DNS,port 53, as required then you can use this method to tunnel DNS.
This is the easiest way (for browsers), if you need it for other tools I'd happily help you to tunnel your DNS requests too. There are many other ways to handle it.
In general DNS anonymity is no threat to most people, DNS only contains hostname,domain and no path or data so you can learn very little through it. (of course you can do a lot of shit if you alter the dns replies on the server, but that would be evil
Cloakfish offers a realtime list of working nodes, about 350-400 at the moment this changes a bit all the time, nodes come and go.
My statistics show that you get about 15,000 different IPs/Identities each month, that's more than almost everyone requires.
If you need more than 15,000 per month then you probably don't need high anonymity for much of the actions, if you still need high anonymity you could use a fast Cloakfish Identity (or even Tor) chained to a large proxylist.
There was a lot of learning involved, Tor is a really complicate project. Cloakfish does a few tricks to increase speed.
As example per default you use only 2 proxies in row, Tor is fixed to 3 and can not be changed. There are also many other improvements and changes to increase speed.
Also the process of circuitfinding was improved and is general faster as a part of the work is done on the servers.
The next version might already include a 1 proxy feature that's already working in alpha stage.
The Cloakfish servers remove bad and very slow nodes.
Cloakfish is always faster than Tor but in the end you are limited by the exit node.
For SEO the best nodes look like a real internet user, those nodes are frequently available but also rarely faster than 100kb/sec (usually 25-60).
So it's up to the user, choose a faster node or choose a more "cloaky" node.
hope that helped to clear it a bit up