People do this mostly in movies but I did it in real life. It was very impulsive.
  1. Ask some questions about the roof. Is it slate? It might be. Slate is beautiful and expensive to maintain. If it's slate, find out when the roof was last replaced. They can last, like, 60 years, but if it's 59 years old you're looking at $15-30k sometime soon.
  2. Find out what kind of electric is running throughout the house. Some old houses still have knob and tube wiring, which is considered dangerous these days.
  3. Check out the windows. Are they original? If you see all wood and no vinyl, probably. Open and close them. See if they stay open. If they work smoothly, someone's been maintaining them well, but if they are in disrepair, they're gonna be drafty. Which means you want to...
  4. Get a sense of what it costs to heat this sucker. Ask for an estimate of all the utilities.
  5. Listen for the realtor to brag about recent updates. It's likely the owners, knowing they were leaving, haven't done anything for a year. Hopefully they were busy before that, because old homes need constant maintenance, and you deserve a head start.
  6. Pay attention to custom details, especially on the exterior of the house and in the interior woodworking and trim. This is the stuff that makes you love the place but you want to make sure it's in good condition, because repairing/replacing it will require more custom work.
  7. Check out the landscaping. I was like, "ivy! I'm in the secret garden! Sold!" But ivy takes maintenance if you don't want to wake up one day with it wrapped around your neck. If there are big, wonderful old trees on the property, you'll have to get them pruned every few years to keep everyone safe.
  8. Find out if you're in a "historic district." This could have implications for your taxes and what you can do with the house.
  9. Accept that everything is a little different in an old house. If the walls are plaster, they may never be perfectly smooth. Your hot water's going to take a little longer. Bedrooms are smaller. But who wants to clean a ton of big bedrooms?
  10. Make sure you are OK with the idea of spending more money and time on housework than you do now.
  11. After you've considered all these annoying businesslike things, find a drink.
  12. Remind yourself of all the things in the house you're obsessed with. Will you be mad if someone else gets to live in this house? Do you have to have this house? If you are 100 percent in love, it'll be worth it. If you are 60 percent in love, it won't be.
  13. If you're going for it, and you're not in a crazy seller's market, make a conservative offer, taking into consideration the money you'll have to spend for any updates the house needs immediately. Be excited. You are buying a house based on love. It almost never happens and you're really doing it!
  14. If you're not going for it, treat yourself to a weekend at a Victorian inn where you can drink wine in front of the fire. Revel in the fact that you don't have to have the chimney serviced. Take yourself to dinner. You just saved several hundred thousand dollars!