Though we're both good with money, we handle bills differently and find it much easier to keep separate accounts. She likes to track everything in detail via spread sheets and pays everything manually, while I simply focus on keeping important receipts, have bills paid automatically, and just check my accounts once or twice a month to make sure there haven't been any errors.
We buy most everything separately, with our own money, and only go in jointly on things on a case by case basis. It's fairly simple so far, and we're happy to keep it that way unless/until it makes sense to change to something else.
We rent, have insurance with a manageable deductible, don't maintain credit card balances, have enough savings to go several months without a job, and tend to live rather inexpensively. The main scenario in which I could see a major expense coming up that could surpass everything one might prepare for is litigation, but if someone gets sued, it's likely better that their finances are separate from their spouse's anyhow. Living in a less litigious society is another option though, and could also help with healthcare expenses :-)
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