Didn't read more than the first comment from someone who was trying to make something far more complicated than it should be.

What we did, was in our shop (separate building, but electricity runs from the house to it). Is we wired a 220 plug (well pump is 220) on the outside of the shop that fed into the breaker box.

So when the generator was plugged in and on, it would feed the shop, which would in turn feed to the house. So you just have to make sure you don't turn on more stuff than your generator can handle. Or turn off some/many of the breakers in the house to make sure other peeps don't turn to much on.

Only thing with this set-up is you have to have a shutoff for the main feed to the house, otherwise you will be back feeding. Which isn't exactly what you want to do. =p
Of course this exact setup would not work for everyone, but the idea is the same regardless.

We have a 5k watt generator and it powers a fair amount of the house without a problem. We do have a propane furnace (tank in the yard). So don't have to worry about the heat part to much.

Well there is my 2 cents...