The common wisdom regarding self employment and health insurance is that if there’s likely to be any health related issues in your future you should think long and hard about self employment. Health insurance can be quite expensive, though there are ways to keep your expenses down enough to make it possible to have it all.
For starters, the most common route is to have one partner continue working for an employer that offers good quality family benefits, while the other person peruses their dreams of self employment. Health insurance premiums for family rates (versus single person rates) are sometimes quite reasonable, depending entirely upon the sort of contributions that employers make and the sort of group rate they’re able to offer. It will certainly be less than taking out two policies.