A Delicate Balance

We're shopping for a house right now. And discovering once again that this kind of thing is always more complicated than you think it's going to be.
First there's the mortgage, and the fact that the myriad of mortgage calculators available online are virtually useless because they never seem to match what the bank seems to think you can afford, nor can they estimate important stuff like property taxes which have quite the impact on your monthly payment.
And mortgage paperwork is insane. Two months records of this, three months of that, last year's this, your most recent that, every piece of identification you have available. Sign here, here, and here. And here. And here. Oh and here, here, here, here, here, no just initial there and there, sign here, here and here.
The timing is also quite crucial. If your lease expires in June, you want to close on a house in June because that way you get to skip any housing payments in July and can therefore use the money for moving expenses, closing costs, etc. So if you start your search early and find a house you like, you end up waiting around until the proper time to make an offer, just so you can close at the right time. But if you don't start searching early enough, you end up being unable to see all the options and possibilities available, and wonder if you're purchasing a second choice instead of "the one that got away."
Sigh.
One day things will be simple. They will.