I have always liked to retire and own a small bar. It will be reasonably well stocked with a few exceptions. The beer will be draft and served in a frosty mug - no bottles or cans - although I will make an allowance if there are local craft brewers. The missus will be the sommelier and in charge of the wine list. I will have a selection of single malts but they will be served neat. Maybe a single cube of ice or a splash of water, but nothing else. There will be music but all selections will be made from my collections ( pre-2000 rock, jazz, blues ) which is mercifully free the ravages of C&W, Rap, and disco. A stage with instruments and sound equipment will be available to anyone who feels making some music. A grill and a smoker will be in the back but there will be a limited selection, since I will be doing the cooking. At the moment the battle is on location. I want the mountains while Ms. DrumBum wants the beach. We have sufficient retirement funds to make this happen so I will keep you posted.
Oh, and any visiting Doper’s drink for free. 
This is an amazing idea. Now I want to do this, too – you take one coast and I’ll take the other. 
I don’t even knit and have no intrest in fabric, but this just sounds so homey and comfy I’d stop by on Sundays just to hang out and drink tea (and nurse my hangovers).
Restaurant that serves weird food
Or a pizza eating business 
Restoring historic architecture. With a dog rescue sideline.
I realize you set it up, but can I kick you anyway? I promise I won’t leave a big bruise, I wear size 3s.
I’ve been thinking lately that there ought to be some way of doing a more self-sustainable version of Rolling Jubilee. RJ, for those unfamiliar with it, buys distressed debt on the open market for pennies on the dollar, and forgives it. According to their current ticker, they’ve used $584,707 worth of donations to buy and forgive $11,694,302 worth of debt.
The problem with this is that it relies on a steady stream of donations to keep going. What if, instead, a similar organization bought debt up at five cents on the dollar, as they’ve been doing, and sent the debtors new contracts that wrote off 90% of the debt, requiring the debtors to only pay off the remaining 10%?
The organization could then use the payments on the remaining 10% to buy up more distressed debt, and do the same thing with that debt. Even if they had a pretty high default rate, the difference between buying the debt at 5% of its face value, and requiring 10% of the debt to be paid back, should make up for that.
There’s a place just down the road from me that raises pygmy ponies.
Bookstore for me too, but I want an old, cozy used bookstore. If only I wasn’t allergic to dust, I might have tried this one IRL.
Some kind of philosophical counseling/consulting business. Kind of like the guys from I Heart Huckabees, but with more of an analytical bent.
Bush Flying and Air Cargo Business serving the most inhospitable areas of the world. If we can land a plane or chopper on it, we’ll get you and your stuff there. Johnny L.A. can run the Rotary Wing Division
Bicycle/Snowsports shop. Summer - bicycles for regular people - no high-end stuff. A section for used/restored bikes as well as new models. Service shop where I can tinker and restore. Winter - ski and snowboard sales and service.
I’d stay in my current business - custom picture framing, but I’d buy a building with a parking lot and fit it out exactly how I want. From flooring to lighting to storage all built to my specifications, no skimping, no slap dash. It wouldn’t have a dropped ceiling! It would have outlets all over the place. I’d have a proper office! And plenty of storage for inventory and window props.
I’d increase the floor space enough to add gift lines.
If it’s an endless pot of money I’ve won I’d look for a building like Sattua described. Or even better, I’d find a bigger place,call up Sattua and have her set up yarn, quilting and tea, which I’d love to patronize, but not run.
I’d also offer gift wrapping, free for items bought from me or as a paid service and also sell beautiful wraps and ribbons.
If the space was right I’d also have a room of real stationery. There are plenty of places to get personalized stationery, but what ever happened to nice boxed letter sheets with just a little bit of decoration? Of course there’d be a selection of fine pens.
Back in the late 90s, before most people had email and when I worked in a gift and stationery shop, I thought it would be nice to have a display that made it easy to assemble letter-writing boxes. Nice wooden boxes including some lap desks, beautiful pens, beautiful paper, stamp dispensers, address books, seals and wax. The shop took orders for personalized stationery from cheap notepads all the way to engraved Crane, so it would have been… sigh perfect.
I’m going to go pet my boxes of un-personalized Crane stationery now.
In 1997 it cost $78 to have a personalized die made, which Crane sent along with your first order, and which you sent back to them every time you re-ordered. And of course you needed one for the paper and one for the envelopes.
My doctor is quite handsome, and more than once, other women have told me, “He could do my pelvic and breast exam any day!” Trust me, it’s not any more fun having it done by him vs. a not-so-handsome doctor, which I’ve also experienced.
Never had it done by a woman doctor, so I can’t compare in that way.
I have a book resale business, and that’s a terrific idea! However, I think it would fly better if you had a schedule; people who go to KOA and other long-term campgrounds would probably like this kind of thing! 
The city where I live used to have one of these! I loved that place; this was how they did things, and they also had pizza by the slice, ordered from a locally owned pizzeria. They showed first-run foreign and art films and documentaries in the evening, and kid-friendly movies early in the day, with the sound turned down and lights turned slightly up. Unfortunately, one of the partners sold out and the man who ran it just couldn’t handle it by himself; he was working 100-plus hours a week and had young children he wasn’t seeing, so he closed it when he found himself unable to find a buyer.
The theater still operates under new ownership; they have shown some locally-produced movies but mostly have plays. “Avenue Q” has been presented there several times, but I haven’t made it to a performance yet.
mrAru and I were joking about winning one of the sweet jebus lotteries and buying an extant sidewalk cafe in Amsterdam in the canal district and reopening it after renovation as ‘Munchies’ - the menu would be excellent emulations of cinnabon, taco bell-esque [tacos, burritos, taco salads and churros] Bojangles [red beans and rice, spicy and less spicy fried chicken, cole slaw, biscuits] and anchor bar original type buffalo wings with blue cheese dressing and celery, and brick oven american style pizza. We jokingly figure all the US tourists there for the weed would get the munchies and keep us in business [also those idiot tourists who absolutely refuse to try local food and insist on McDonalds everywhere.] Oh, and I understand that there was a guy in K-town who tried opening up an american donut place like Dunkin Donuts and so there might be an old school Dunkin Donuts fryer lurking, if so we could add sinkers and american drip coffee, and the old early 900s drip iced tea using that tea bunn type machine that some fast food places had.
I couldn’t run a used bookstore. I’d always be pulling books off the shelf and keeping them. I’d be bad enough in a new bookstore with always ordering an extra copy for myself of most of the books I was selling.
I’d find a beautiful place, probably on a beach, far away from mainstream tourism, and build an amazingly funky hostel/ guesthouse where people could stay for next to nothing.
I’d run a large classic arcade, beating Funspot in New Hampshire in total number of machines, except mine would be all classics. (Pinball and other electromechanical skill games through the mid-90s, video through the early 90s.) No prize games, no Skee-Ball, no kiddie rides, no go-kart or Laser Tag or mini-golf or whatever. No attached pizza joint, though if I were smart, I’d try to lure some casual restaurant franchisees to establish nearby. It’d be more an interactive arcade museum than an amusement location. Establish in a decent area of a mid-size city, like Indianapolis or Louisville. It would have conference rooms and meeting halls to cater to enthusiast groups or classic gaming conventions. I’d also hire a full-time staff of buyers and restoration/repair guys, paying well enough to lure the best folks possible.
Or, run a classic home video game/computer game fan company that provides parts for homebrewers as well as bankrolling and selling complete projects. There are already a number of places selling bare circuit boards, or empty cartridge shells, or offering a handful of homebrews or whatever, but typically of limited extent. This would be a full-service company, offering everything from parts to total publishing packages for all of the systems. Custom circuits, professional manuals and boxes, and so on. I’d finance, produce, and publish for the current crop of programmers and developers, and if a programmer expressed interest in doing a licensed game (hey, I’ve figured out a way to do Mappy on a 2600), I’d pursue the license so that the product would be an official conversion.
(The above is a bit odd since I recently got rid of my classic game/computer collection. But hey.)
A truly independent local art theater. I would just be the money man for this one. Indianapolis used to have a good independent art theater on the south side, but it got out-financed and run out of town by a chain, which promptly stopped showing art films after they won. The guy who ran the indie theater has been in the field for years, and is currently running an art film program in another town… I’d love to lure him back, have a theater custom built to his specs in a better part of town than his old theater had been, and give it to him to run without worry over finances or popularity.