There are ways to prevent disappointment. First of all, don't hesitate. If you see a great property, make an offer quickly. Try to make the offer as clean as possible--assume that, in this market, there may be other contenders. Don't put in contingencies that you can live without having. Match the seller's dates where you can. We see so often that people insist on things, and then don't get the property, after which they say that they would have given in.
I always tell people to make the offer that they would be unhappy to hear that someone else got the property by making. If you are going to say later that you would have gone higher, then do it upfront. If you have other access to cash, to make a better offer, don't wait to pull that out. Go all in. When listings are in short supply, and they are in Connecticut, that's called a seller's market. If you are the buyer, that means that you are not driving the bus. Accept that and act accordingly. You can even consider writing a letter about why you would be the perfect buyer, and how much you love the home. It has been known to do the trick on occasion, and it can't hurt.
Don't offer what you can't afford, because you are wasting everyone's time, including your own, but be realistic. Your parents, or other sources of advice, probably bought their first homes when interest rates were very high, and they may not be accurate on the cost of money now. Be sure to get preapproved, so that you can react quickly if necessary. If there is a counteroffer, be prepared to answer almost immediately. You need to know your top price, just the way you would if you were bidding for art at an auction.
And, if you still don't get the property after following the advice above, don't waste time on regrets. You did your best, and it is what it is. Move on, and find the home of your dreams next time.
