First, I like to find the shittiest shitholes I can find. Anything that sells for less than $10,000 is a good bet. Urban ruins, ex-meth labs, abandoned farmhouses - all of them are fun for the gawking! In a way it's sad, because you can see that at one time someone built this house, with hope for the future, and they tried to fill it with love - but something went very, very wrong along the way, and now look at it. Look at it! Then I make up stories about zombies living in the cupboards, and poltergeists.
Then, I do what I call "backup planning". If Phil dies, I probably won't be able to afford to live in Orange County anymore. Even if I get a good paying job, it's very, very unlikely that I'll ever be able to earn a Phillip-level salary, and you can't make it down here on one Dana-sized income. So I look in more affordable cities, like El Paso and Portland and Memphis and choose which houses I could afford with the life insurance payout. These searches are not that interesting, and they're sort of macabre, but they fill me with reassurance that I won't wind up an impoverished widow, wandering house to house, begging for alms in a shawl.
Then comes the funnest search. Rich people houses.
The best place to look for rich people houses is Sotheby's International Real Estate Listings. There you can find castles, private islands, houses that have jet-landing-pads, etc. These are fantasy fodder, and I spend way, way, way too much time searching for them.
Here's what I've learned about rich people in different countries.
Greece is the place to go if you want something quirky, bohemian and special. It is the place where I found my dream house - a seventeenth century castle, decorated with colorful floor cushions and rustic window seats, overlooking the mountains. Someday, when the revolution comes...
Hong Kong's upscale real estate market is blindingly expensive - way more expensive than anything I've seen anywhere else. And yet, every building is the same - bland, beige boxes with black accents and large windows with water views. That's it. It never changes. And it pisses me right the fuck off. Because if you are going to spend 25 million dollars on a house, why would you buy a boring ass box, when you could afford something truly unique and special? You're basically throwing your money into the street, since you could get the exact same thing for 500k in the suburbs in Orange County. Fucking beige boxes piss me off.
Dubai has extremely fancy luxury houses, with lots of bells and whistles, but they all look like they were designed by lecherous hairy men from Las Vegas who wear gold chains and leave the top three shirt buttons unbuttoned, and leave "tasteful" porn magazines out on the coffee table.
The Caribbean has lovely ocean-view homes, but for some reason, all the houses have cutesy names that make me want to vomit. "Deliliah's Delight", "Shannon's Shack", "Shelly's Seashell Staycation Sensation". Someday a hurricane will take them all out.
The USA actually has a number of very tasteful, elegant homes, though it also has its share of beige boxes. The best homes tend to be on the east coast and in the south - large, sprawling mansions with columns and turrets and Victorian embellishments and private lakes. These homes also have names, but they tend to be more sedate and classic sounding. "Biltmore Estate" and "Vandergraff House" and "Irving Farm".
After I do my searches, I get to planning. What would I buy, for instance, if I won the powerball and I was a billionaire and could afford anything? Would I just hire an architect and buy some land and go crazy with secret rooms and hidden passageways and a trampoline room? What would I buy if Rosemary's Baby Daddy gets published and sells really well and I could afford like, a million dollar house? What would I name my beautiful house? Hammer House? That's terrible. It sounds like a construction project, or a jail. Dana's Den? I would rather be homeless. The Cotswalds? Already taken.
I get frustrated when I can't pick a decent name for my imaginary house, because it makes me feel inferior. Like I'm no better than all those rich people I just judged so harshly. Like I don't deserve a fancy house any more than they do. I don't like to think about myself that way, so I just decide that naming a house is silly and pretentious, and that my imaginary house doesn't need a name. It just needs me.
Then I look up shitholes until I feel good about myself again.