I think the questions you ask apply to non-cloaked pages as well as cloaked, so you might get a better response over in the Search Engine Promotion [webmasterworld.com] section of the forums... I can answer some of your questions tho:
Hi foxtrot, yeah sorry, it's been kind of quiet in cloaking lately. I think a lot of cloakers (and I personally know that the technique is very popular) don't like to admit they practice it.
I think the questions you ask apply to non-cloaked pages as well as cloaked, so you might get a better response over in the Search Engine Promotion [webmasterworld.com] section of the forums...
I can answer some of your questions tho:
So your site is being crawled. That's good... the SE's know you exist. It isn't really an indicator of success, though. I've seen heavy crawling on sites with poor or non-existent rankings. Crawling is not always followed by indexing, especially if duplicate content is found.
You should not expect improved results in search engine rankings based on whether a site is cloaked. Cloaking is mainly a defensive technique to keep pages from being page-jacked (old-school) or scraped.
Domains with cloaked pages have the same chances of getting rankings as non-cloaked pages. In fact, the last thing you want is for your cloaked pages to have some distinction from non-cloaked pages (and what could give them higher rankings except some kind of distinction, right?).
The fact that you are seeing the pages in supplemental indexes is actually encouraging. New domains often appear in the supplemental index (Google's "sandbox") until they age for awhile and/or improve their "trust factor" through incoming links from trusted, on-topic domains.
You can try to avoid the sandbox for your domains by purchasing "aged" domains that have been registered and active for awhile. If you can do so and maintain the original theme and incoming links, you may be able to keep the original Pagerank of the domains, and keep or improve the domains search engine rankings. Of course, this may not be economically feasible.