Are they REALLY not giving you any good advice? Or are they just telling you what you don't want to hear - that the house is not worth as much as you think?
probably.
But what if it doesn't sell for 290? What if it's not about the price but the market?
It's never "not the price but the market." In other words, if the market is terrible then the price must plunge in order to sell--but it will sell if you price it low enough. If you can't price it low enough (i.e., if you owe more on it than it's currently worth), then your only options are (1) short sale and (2) be stuck with it. But there's a massive, massive distance between what you owe on it and what it's priced at--that's the margin within which you have to move, in order not to be stuck with your one-hour commutes and bad schools.
What price have realtors suggested recently?
By the way, I'm not a fan of the "drop it by $20k increments" approach. A good realtor should be able to tell you how your market is, but in my area, doing that makes you look desperate (which you are, but why show it?) and invites lowball offers. In my area, the strategy would be to take it off the market, get the best realtor around, tell her you want it sold in X time and ask what price it would need to be at and when you should put it on the market. (She will probably say to wait for spring, timing-wise, and it certainly looks way better on the "we're NOT desperate" scale to take it off the market for a few months and then put it back, rather than leaving it on the market at ever-lower prices.)
Everyone I know who had to move is either stuck with two houses or had to do a short sale.
...because they owed more than it was worth. That's not your situation.
It's not that we're not listening. We're just reluctant to lose money on it.
Too damn bad. That's what happens when you buy at the height of the market. I feel for you--I've had dear family members in your situation, and it sucks--but after five years of this, you just have to face reality.
I tried to do my own calculations: original price + inflation - depreciation + cost of improvements = $310K.
That's not the right calculation. When you start with a normal house (as opposed to some handyman's special that a house-flipper might buy), you almost never get back the cost of the improvements you make to your home. Best-case scenario, for certain improvements (e.g., a well done classic or trendy kitchen remodel, or a fresh coat of popular paint colors throughout), you might get 75%-88%-ish back. In other words if it cost you $10k, you might get $7500-$8800. And those are the highest-return improvements you can make. Improvements don't pay you back what they cost or more unless you took a handyman's special in a great location and turned it into a fully updated and nicely finished home.
Besides that there's also a fear that the housing market will bounce back to what it was in 2007 and then we'll have lost a 100K by selling it cheaply.
What's it costing you, in dollars, to have one-hour commutes? What will it cost you, in dollars, to put your kid in a private school (and commute to that school) to make up for not having good school options where you are?
And more crucially, what is it costing you in terms of TIME taken out of your brief span here on earth (are you going to look back on your deathbed and fondly reminisce about the thousands of hours you spent commuting, instead of with family or doing things you really enjoy)? And what's it costing you in stress? Only you can put a price tag on it, but it certainly has a price. A big one.