Regarding healthcare, the Affordable Care Act which goes into effect Jan 2014, eliminates:
- the need to be employed to have healthcare insurance
- being turned down for healthcare insurance due to pre-existing conditions
There are no asset tests. It will be more expensive than employer-subsidized insurance, of course, because you will pay 100%. But at least you know you can buy it.
On assets required to retire, check out firecalc.com. As posted elsewhere here, the younger you are at retirement, the more safety margin you may need to have. If you expect to live to 90, 55 years is a long period to fund safely.