Is it worth rolling the dice when you flew into town to find a home?

Whether working with sellers or buyers,I often get the comment,why don't we "try this list price and see what happens" or "let's try this offer and see what happens".

I will listen to the home seller's/home buyer's logic and reasoning for any price they want to offer. I will gather as much information about the home,the community and any "inside information" that may impact the price point....such as if another like home is coming on the market/I was told that another buyer looked at that home and also registered an offer. Whatever my client wants me to list their home for sale (or rent for) or purchase (or rent for)I will do and at the same time will tell them to temper expectations if the number is not consistent with the market/the inside information I have.

I took a client in town from Florida,relocating to the area for a job. I contacted a listing agent to register my client's offer on a home in Silver Spring just off of University Blvd. that we were going to write and that the offer was about $10,000 less than the asking price. When I talked with the listing agent, he told me that 2 other offers were coming in.
I conveyed this to my buyer to show that there was obviously other people interested in this beautiful home,with the home being on the market only a few weeks and receiving multiple offers,there was a chance that one offer would be full price. There is also a chance that the other people will make lower offers and/or not look as strong financially in which case the offer could be accepted. So,did my client want to re-think his offer or was he happy with his offer?

My client told me to roll the dice and stick with his offer,which was a pretty good offer, and if they come back with a counter offer we'll go from there. He flew back to Florida to resume packing with his wife and family for the big move. I got a call last night from the listing agent that one of the offers was full price and that the person was strongly qualified,so the owners will work with that offer and thanks for my efforts.

My client was let down,but ready to move on to the next home. So he is going to fly back into town next week. Will his next offer be full price? I don't know. It depends if the place is priced well. I'll show him the comparables,talk about what happened last time and see how he wants to play it.