The price question comes down to whether or not we are in another 'bubble'. Sure, prices are going up but they're coming off some pretty ridiculous lows. In many areas, the prices are still 30% or more below the 'frothy' highs.
In the days of the real bubble, everybody bought a house with the intent to sell it later for more. But not much later because they had ARM loans with increasing interest rates. As much as the buyers were greedy, the banks were worse!
The "greater fool theory" didn't hold up and there were no buyers and the loans were getting more expensive and people just couldn't afford the house. Had they been realistic, they couldn't afford it in the first place. Then the government doubled down and cancelled the taxes on the 'gains' of the short sales. This allowed everybody to just walk away without owing tax on the mortgage amount minus the short sale price. Since there was no penalty, a lot of people walked away.
The idea of Freddy Mac and Fanny Mae making risky loans started under Reagan and later spread through the entire banking industry and we all know how that worked out.
We are still seeing ARM loans and these simply shouldn't be allowed. Even Greenspan made comments about the risk of these loans.
In the end, there's only so much dirt and we're not making any more (except China and Singapore). Owning a piece of it is generally a good thing. For one thing, you build wealth (equity) at a far better rate than you can get on most low risk investments. In '86, I bought a small house for about $80k. In 2003 I sold it for $290k so I made a decent return. In 2006 it was offered back to me for $130k so timing is everything. The point is, I had a place to live for 17 years, no HOA, virtually no maintenance and I made a few bucks out of the deal.
So, look at buying the more expensive house but try to make sure prices haven't topped out. I live in California and prices never top out - well, hardly ever.
I didn't play with the numbers but would the house be self-supporting if you had to leave the area and selling wasn't an option? It's one thing to take a paper loss, that is, losing theoretical equity but it's quite another to lose real money!