In these Troubled San Francisco Times, there is a lot of talk about who was here when, and what that does (or doesn't) mean. In an effort to both assist newcomers and take long-time residents down memory lane, we present to you Ask a San Francisco Native, a column penned by SF native and longtime SFist contributor Rain Jokinen, which is inspired by a similar one on our sister site Gothamist, and is intended to put to rest all those questions only a native of this city can answer. Send yours here!

Dear Rain,

If you won the lottery and could suddenly buy a house in any San Francisco neighborhood, where would that be? Why?

Signed,

Money Dreams

Dear MD,

I've been living in rentals my entire life, and owning a house here has long fallen out of the realm of possibility for me, so of course I have fantasized about winning the lottery, and buying all kinds of places (and not just that condo complex I want to replace with a dive bar).

I've dreamed about buying an apartment building and then renting it out to all the family I have who have are also lifelong renters (some of whom have had to leave the city for cheaper dwellings outside of the state). In those dreams I could get away with charging next to nothing. (This is a fantasy, I don't have to worry about taxes and upkeep, remember?)

Then I'd buy my parents a house, something with a view, and a garden, wherever they'd like. It would most likely be somewhere on Potrero Hill, where they currently live, since they appreciate the somewhat isolated feel of the area. Or maybe they'd want to change it up, and live somewhere where you can more easily walk to restaurants and movie theaters...

And then I'd get to choose MY house. And you know what? It wouldn't be a house!

I've lived in apartments my entire life, and I've realized it's what I feel most comfortable in. Don't get me wrong, I understand the appeal of having a huge space, and multiple floors, and not sharing walls with neighbors.

But I also kind of dig being surrounded by other people; there's something about it that makes me feel more secure. Plus there's free entertainment when your neighbors fight! (I'm talking to you, downstairs neighbors who were fighting again last night. Next time, do it louder, so I don't have to lay on floor to hear it clearly!)

I'd want to be somewhere with history, so nothing built in the last 40 years. I'd like a place with a panoramic view, so it would probably have to be a neighborhood on a hill. While I'm not too keen on maintaining a garden, it would still be nice to have access to some outside space, so maybe something with a nice deck. Stairs suck, so toss in an elevator. I'd have a parking space, but I still prefer being able to walk to my favorite places easily, so nothing in the outerlands.

All those things considered, and I'm probably looking at a building on a hill. Factor in my love of movies, and it all adds up to an apartment in the famous Dark Passage building on Montgomery Street on Telegraph Hill, one of which — alas! — was sold earlier this year.

But if I've won't the lottery, I can probably convince someone to leave with a little cash incentive, right?

Also, how much lottery are we talking here? Like, a billion dollars? Or just a couple of measly millions? Because ideally, I'd buy that apartment, and then buy an actual house somewhere else, like Palm Springs, which I could then rent out as a vacation spot when I wasn't there. (Especially during Coachella — I'd rake in the dough then!)

And why not toss in a nice little beachside shack somewhere in Hawaii, and a studio apartment in New Orleans? I'm assuming I have enough money to just venture from place to place all I want for the rest of my life, right?

So, in summation: A couple of measly millions: An apartment in the Malloch Building in the city. Billions: Homes for my family, that art deco apartment for myself in SF, and some vacation homes in my favorites spots.

Man. Being an imaginary billionaire is the best!

Now, if you'll excuse me...back in the real world, I'm off to warm up the final slices of the leftover pizza I've been eating for the last three days.

Rain Jokinen was born and raised in San Francisco and, miraculously, still calls the city home. Her future plans include becoming a millionaire, buying a condo complex, and then tearing it down to replace it with a dive bar. You can ask this native San Franciscan your questions here.