Last week, on Tuesday night, about a thousand people gathered in 10 cities to for Meet, Plan, Go!, the annual career-break event. Here in Minneapolis, yours truly served as moderator for a panel of recent returnees—and also manned a table labeled “Prepping the Leave,” along with Leif Pettersen, accomplished travel writer.

Dozens of travel enthusiasts visited that table and pelted us with questions. Here are five pretty-good queries and brief answers…

• We hope to leave early next year for six months or a year. We have a house—and can’t decide whether to rent or sell.  Any advice?

That’s easy: Hold! I mean, if you try to sell your house in this (or any) market, you may lose control of your timing, since so many things can go weird or wrong. Plus, prepping and selling a home can take dozens—hundreds?—of hours. You need that time to plan your trip.  Stay focused!

Not to mention, where would you live when you came home? Another conundrum, right? Why not come home to sweet home. You can always sell then. Find a good renter or house-sitter. Now get outta here!

• I might want to stay longer in my destination country than their visa allows for. What to do?

That’s a common desire, and there are ways around it—but (as they say about investing), you’ll have to determine your own risk tolerance! In some countries, they legislate such laws but hardly enforce them, unless, of course, you’re causing trouble. I stayed too long in Italy once, and they kept taking my money.

In other countries, you might leave to take a mini-sabbatical within your sabbatical. Case in point: Many people retire in Mexico, but visit the States for a week or two every six months or so, just to get fresh passport stamps.

• What are some tips about credit cards, currency translation fees, cash, and such?

That’s another maze, thanks to the banks and constantly changing realities and regulations. But here are a few tips that might work: Use a debit card to get cash (lower fees); in many countries, vendors appreciate being paid with cash (tech issues + tax avoidance?); use a credit card with no translation fees for purchases (check out Capital One and Chase Preferred); seek a credit card that gives cash back, since you’ll likely be spending; think twice about airline loyalty cards, since they’re rather like the nickel—ain’t worth what they use to be.

• I’m quitting my job for this trip; what about health insurance?

You will probably be able to keep your existing policy for 18 months, thanks to COBRA legislation. Do that, and you’ll also have coverage when you get home. For those without insurance, getting a high-deductible “catastrophic” policy might be a good idea—in case of a worse-case. But know this too: Many countries provide decent healthcare for free or cheap to visitors. For peace of mind, though, do some thorough research and avoid taking chances that may stress your big break.

• What do you pack that I might not think of?

What else? A good pocket knife. Nothing too huge, mind you, but one with knives, a tweezers, a toothpick, and (above all) a bottle opener and corkscrew.

Cheers!