[pasbesoin]

A thought: If they want you bad enough and you are in the U.S. or similar, make continued healthcare coverage and maybe some other benefits part of the negotiations, even if you go contract. (+)

Sabbatical? Some companies will offer/support that kind of a time off model.

Guard your IP.

+ I'm not certain this is possible, but I've heard sometimes vague descriptions of such arrangements. It seems to me that staying within a larger pool would be preferable to purchasing independently.

[noodle]

most freelancers include healthcare/insurance/taxes/etc. into their hourly rates by default. not all, but i think its reasonably standard. in the US, that is.

[pasbesoin]

For health insurance, is there a benefit (so to speak) in staying within the former employer, now client's pool, as opposed to shopping independently? I don't know much about this and what is possible. I've heard mention in the past of some people achieving such an arrangement. Whether that information was correct, I am uncertain.

EDIT: I updated my prior comment, above, to better reflect my uncertainty.

[noodle]

yes. it will almost definitely be cheaper in total with your employer (i'm not taking who actually pays -- you, your employer, or both).

going solo, it will be more expensive unless you can get in with a group of some sort. for example, you can join up with the freelancers union and get help with your rates (i think -- haven't actually done the work to see whats cheaper).