For listings to sell in this market they must be right-priced. If this describes the homes you favored, it is not surprising that another party was simultaneously interested in them. Plus you're looking in an ascending neighborhood in Bucktown. The only measure one might take of your agent is how he/she "set the table" for you. By this I mean were you cognizant that you needed to make the strongest offer straight away?
What I tell clients in situations like this is "how much will losing this home hurt?" Then we translate this sentiment into a price tag, whether it's $500 or $5000. But this amount can be solely determined by the client.
I bid you good fortune and wise counsel as you proceed.
The Real Estate Lounge Chicago
Depending on the property and its value, the list price may have been undervalued to the market and someone paid full list price or even more. Your agent should be able to determine the value and then together you can decide what the right bid should be.
One of my clients was just involved in a 5-way bidding war for a property in Old Town last week but they had to pay over the list price to get it. Even in this market, for the right property there can be several interested buyers.
Also today it is more important than ever to be pre-approved for a mortgage through a reputable lender. I mean full pre-approval meaning you have already give all the documentation to the lender. So many pre-approvals I see are really pre-qualification letters and only slightly better than meaningless because they only based on a credit check and what the buyer says their income is without any documentation.
I often recommend to my sellers that they not accept offers until the buyer has been run through the mortgage lender's automated underwriting system. As a buyer you should have your lender do this for you. It will make you stand out in a crowd of only pre-qualified buyers.
Know the true value of the property, which may be less, the same as, or even greater than the listed price. If the houses you wanted were significantly underpriced, then perhaps an offer even higher than the listing price would have been appropriate. Keep your offer at or under what you determine to be its value. But adjust it, as Tom suggests, based on how much you want (or can live without) the house.
And try to get feedback from your Realtor on how you could have strengthened your offers on the properties you didn't get.
I would suggest evaluating your approach to offers. No contingencies is great but it's not the only item sellers are concerned with. Many sellers are wary of contingent deals in the current market, but they still fly, especially if the buyers agent for the contingent offer does a great job presenting the offer, and pricing the property that needs to be sold. The seller will take a hard look at what the buyer has to sell, and gauge the risk. Real estate sellers are very complex and every seller weighs the facets of each offer differently. If the seller does not NEED to sell, they may favor a contingent contract over a less competitive contingency free contract.
As far as your agent is concerned, he or she should be giving you accurate feedback as to why the other offers were accepted over your offer.
For example, How much earnest money were you placing on the deal? This is crucial to making your offer more competitive.
Is you closing date attractive to the seller?
You should also appeal to the seller's sense of pride in their property. If there is something about the house you love, make sure you draft a letter to the seller letting them know why you want their home. Small personal touches help you stand out in competitive situations.
I agree with Jim Roth in that your agent is definitely getting you into the hot properties (as demonstrated by an 0 for 2 record so far), so it is likely they are doing a fine job.
Good luck. If it's meant to be, it will be.