This is part of my current dilema. As I have mentioned around here the long term Chez Haus goal is to buy some land (probably 20-50 acres) out away from town, build a house and a side home for my mom to live in. The funding is the question. I have my home (almost paid off), and my mom's home (paid off since the mid 70's) here in Dallas. I could sell them to pretty easily finance this goal, or I could turn them into rentals, and finance the farm.
Problem is how much I could sell them for is dropping, and how much I can borrow for is going up in cost. My hopes at this point are for a crescendo in real estate price pain (i.e. a real crash), then buy cheap so higher interest doesn't slaughter me and I can use the two houses as rentals to offset some/all costs. Just don't know if I'll get that lucky with the timing. I have enough capital right now in reserve to drop a sizable down payment on said farm if I didn't want to sell the current home, which would still be optimal as having a place to live while building a house and all.
I have a friend who just got married, it entailed her moving to her "dream city" of NYC to live with her man. They were buying a condo there while interest rates were going up and it was killing them... And now she's trying to sell her house in Dallas and has already had to drop price on it once so she's getting it, as they would say, coming and going right now. She's owned the house just long enough that I think she's still going to be profitable on the transaction, just not as profitable as she would have liked.