Stop obsessing?

So as you know I spend way too much time thinking about and researching travel - both the trips that I actually take and those that I just dream of. Obsession or hobby? I think it's a little of both.

My latest project is planning our family trip to the Florida Keys in early July. So far I've made the biggest two decisions: booked our airfare, and the bulk of our nights in Key West. I got a great deal going directly through the hotel, and found a two bedroom/two bath full size condo complete with washer/dryer. This should be a fabulous set up for three adults and one child for the week. So what's left you ask??? The other two nights.

We'll fly into Miami and then have one night on each end in the city before our travels to and from the Keys. I'm determined to get the best value for our money and figure that I'm planning early enough to watch all of the deals. So far this is paying off. I've been watching car rental prices (also have to book this one) through Hotwire.com, Orbitz.com, and Travelzoo.com. When I began tracking prices several weeks ago, the cheapest rate for the nine days for a full size car was $400. Tonight I found $218, and I hope it continues to go lower. The question becomes when does one stop gambling and commit? It's hard to say, but I think I'm close.

I seem to be a lot further away from the elusive one night on either end hotel deal. I'm pretty sold on a Best Western (three star, of course) for the first night that includes a very well-rated breakfast buffet. I always try to get breakfast included, and more than just an "OJ and a dry doughnut" as my husband says. This concession is for him. I'm certain I've found us a good deal through BestWestern.com but have yet to commit.

As for the last night, this one really is troubling me. I've decided that I will put us on Miami's South Beach for the night, but the choices are endless. And between Priceline.com and Orbitz.com there are some great deals to be had. I just can't seem to decide on the best value. I keep coming back to a Courtyard by Marriott that includes breakfast and two queen beds plus sleeper couch for the little one, but then I keep wondering if I'm missing out. Will I get there, look around at other properties, and be disappointed? Too many choices! Does anyone out there have any recommendations for SoBe???

There are simply so many choices! Obsession or hobby? Perhaps a little of both.