We are planning a trip in a few months, but unfortunately the available quality redemptions right now for places we want to go are few and far between. However, just doing a bunch of close-in searching reveals a plethora of options as we don't really have a firm destination set in mind, so the thought occurred to me that we should just wait until we are a couple weeks out and start looking for good options to travel from essentially NYC area to anywhere that peaks our interest and has a good redemption for business or first, then figure out accommodations, etc. While at our destination we would figure out the return flight and, possibly, book a cheap repositioning flight to get to the return flight. For example, it looks like there are several days next week with LH 1st award space from JFK-FRA so we could theoretically transfer chase/amex to aeroplan to book, find some EU hotels or airbnbs in various locations and train it between where we are staying (since we like to take trains around Europe, generally). While there, we could keep an eye on return flights to the US west coast and book the return flight and any repositioning flights on either end. I think this is totally doable but my wife, who likes everything planned in advance, has doubts. I think that with a load of flexible miles (chase/amex) this plan is easy to execute and low risk. Does anyone have similar experience doing something like this? I would be curious of anyone who has tried this and hit a snag.