Recently in my office I listened to a story about a Buyer who had just missed out on the house they wanted to call home. How? They waited several days after the home came on the market and by the time they wrote their offer, someone else had beat them to the punch. I think in today's market it is easy to over-strategize or get lackadaisical and forget one of the fundamental rules in real estate: "time is of the essence".
Even in today's slower paced market if you identify the home that fits you and your family, you still must move quickly. If you are interested in a house, there is a chance that someone else may be too. Often in today's market people hesitate to write an offer immediately because they do not want to pay full price. I understand that. However, if it is a home you really want, I would suggest writing your offer immediately. Simply make the offer that you feel is appropriate for the home. At a minimum, it shows the Seller your interest and raises the likelihood that you will be involved in negotiations on the home, even if there is another offer.
If you decide to hold off on your offer and are willing to take the risk of losing the home to another offer, be sure that it is over a dollar value that you can live with if you lose the home. If you are buying the home for the long term (as you should be) maybe a $10,000 to $20,000 reduction in price is not as important as getting the house that feels like home.

Jason, everybody wants to get at least a fair deal, and nobody wants to get a raw deal, but your last point is - or should be - the most important point of all.
Whether you're buying a $150,000 studio condo or a multi-million-dollar manse on the water, however "good" the deal is, you're overpaying if it doesn't feel like home.
And truly, if you can afford it, then you should not let your desire for a "great deal" get in the way of getting the home you truly love.
"Home" is not a parcel of real estate, it's the stage setting for our lives. It's where we wake up, fix breakfast, brush our teeth, love and argue and entertain and relax and worry and all of the things that make up a life worth living.
Is it worth saving $25/month on a mortgage payment to settle for "second best?" You've got to reconsider the value you place on your personal happiness if you answered, "Yes!"