Decision-making time - again?

A quick and dirty update on the long saga of house hunting that I have been sparing whatever readership I have left from:

January: I contacted a realtor to see a couple places in Bridgeport, which I went to see with Audrey because Dan wasn't ready to look yet. Those were a flop, but the realtor seemed like a good guy, so we kept in touch - him sending me properties that fit our criteria, and me, for the most part, vetoing them.

February: Dan joins the search party, and we begin to look at places in earnest as our lease was going to be up at the end of May. Things seem to be going slowly but steadily, though nothing really sparked our interest.

March: more of the same.

April: A nice 2-flat came on the market, Dan and I put in a successful offer and were ready to buy when 3331 Lowe showed up. 3331 was a cute brick number on the street we currently rent on; it was dated and needed some work, but overall it had a ton of potential. We made an offer, beat out a competitor, and eventually had our offer accepted - or so we thought. A couple days later and talks start going downhill. All the sudden the seller doesn't want to use the dates she had previously agreed to because they are too soon - keep in mind that any later date will cause us to be homeless in the interim. Seller refuses to cover our storage and housing costs for this homeless period and seemingly re-agrees to our dates. Hours later, she backs away completely, telling her listing agent that it is simply too mentally and emotionally taxing to sell. That same day she shows her property to other people - days later it is under contract to someone else.

May: We manage to extend our lease on a monthly basis on the understanding that we will give our land lady two months notice, and will not leave after August if we haven't told her we were intending to. We continue to look, this time in Oak Park because no properties have hit the market in Bridgeport since 3331. Oak Park begins to look great - loads being listed - historic, lots of land, tons of room, etc. We put an offer in on our dream place, but are told that there is already an offer in that is higher than we think the place is worth.

June: Time is ticking. Found another place that is very much like 3331 Lowe in terms of charm and potential. Put in an offer, got a reasonable counter, and were hours away from signing. Call comes in from our realtor the evening before we sign that he had heard from the listing agent from 3331 - she has a dark horse contender. We are given the option to preview a place that hasn't even hit the market yet in Bridgeport (this apparently happens a lot - things sell there that never officially hit the MLS). Tonight we see this place, and go back to see the Oak Park place - it's decision time about whether we stay put, or move on. Space or location; city or burbs. This may seem minor, but it's anything but - it's a shift in lifestyle that Dan and I have to jointly decide to make - or not.

Here we go.