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Lebanon wouldn't be such a bad place to buy a house, what with the new hospital being built and Western possibly expanding the school. A lot of the houses there were older though, which means potential issues with lead paint, inadequate wiring and poor insulation. You are correct in that finding the right house in good condition for the right price is a real chore. Any house you do buy will end up being a compromise in some way.
On the other hand, you can't look on renting as paying money and getting nothing to show for it in the end. You need a place to live, and that is worth spending money on, just like you need food. I'd guess that if you crunch the numbers buying will be somewhat better from a purely financial standpoint, but it's up to you to decide if the benefits of owning are worth the hassles.
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It's always better to buy than to lease, as a home is an investment (same thing w a car. WHY DO PPL LEASE CARS?)
If we are able to get a home, I think the basic idea I've been getting is that it's probably better to get as new a home as possible and keep it as modest as possible to keep the debt down.

Just like xffan, we are so sick of renting. In the past six years of marriage, the last three of which we have had our daughter, we have always lived in a basement apartment. We're so ready to stop being "trolls" (living under people) and would LOVE to have our own place.
I think I'm going to fill out some paperwork with our bank and see if they would approve us for a loan. All this is pure speculation until I know if they'll even give us a loan while we're in school with no income besides the HPSP monthly stipend. I have heard about the VA loan, but don't know if that's something that's available to us before ever having done active duty.
If we are able to get a home, I think the basic idea I've been getting is that it's probably better to get as new a home as possible and keep it as modest as possible to keep the debt down.
One topic I haven't seen mentioned much is the closing costs of selling a home when you are done. If you buy a house for undergrad, move, buy a house for med school, move, buy a house for residency, move, and then buy to settle down someplace, all you will have to show for your "investments" is a very wealthy real estate broker.
If the decision is being made purely on financial grounds, the New York Times has an easy to use buy vs rent calculator -
http://www.nytimes.com/interactive/business/buy-rent-calculator.html
As we have seen in prior posts in this thread, there are a lot of non-financial extenuating circumstances like pets, home maintenance skills, desires to modify, home sale skills, etc that will also affect the decision of whether to buy or rent a house.
It sounds like buying is the right option for you. If you have good income now I would try to get prequalified for a loan now and never mention that you're planning on going to medical school. Banks don't like loaning money to people without income anymore. I couldn't get a home equity loan on my house without proof of income even though I own the house outright. You can't get a VA loan until you've been active duty military.
One topic I haven't seen mentioned much is the closing costs of selling a home when you are done. If you buy a house for undergrad, move, buy a house for med school, move, buy a house for residency, move, and then buy to settle down someplace, all you will have to show for your "investments" is a very wealthy real estate broker.
I know a lot of people who bought houses just before the real estate market fell on its face who would disagree. There are definitely some risks to buying a house as an investment. I don't think the OP will have to worry about property values in Lebanon declining, but between closing costs, property tax, home improvements and insurance, buying a house can be an expensive investment, and potentially a losing one. In the OP's case I'd guess that buying will be better than renting from a purely financial standpoint, but I'd definitely want to crunch all the numbers before doing either one.
Leasing cars makes sense if you want to always be driving a new car. After driving a leased car for two years or so, its relatively easy to switch to a newer leased car. Lease payments are lower than purchase payments, so you can get a nicer car for the same monthly cost. If you buy a new car, its worth much less the second you drive it off the lot. If you bought the new car on credit, you're immediately upside down in a loan. You don't build equity through a lease, but you do get to drive a nice car for less hassle and lower monthly costs. As for me, I'll keep buying cheap crappy cars like my current ride, a 1989 Toyota truck with the legendary 16 1/2 RE engine (a 22 RE engine running on three cylinders).