Our goals were:
1.) Go to places we hadn't been to before. (we live in Boston and we've already been everywhere in the northeast, so excluded the entire northeast.)
2.) Go to places we wouldn't otherwise visit. (for example, I would never buy a plane ticket and make a special trip to Mount Rushmore, but if I'm driving through the area I'll definitely stop. If it weren't for this trip I'd probably never go to places like South Dakota, Iowa, and Montana.)
3.) Go to games at as many baseball stadiums as possible. (we saw 10)
I think it would get overwhelming. I could just see it: "okay, only 67 more days to go!"
This hotel is incredibly hard to book. It would be next to impossible that you would ever be able to book a one-night stay - they have two and sometimes three day minimums. I have tried for years (plural) to book rooms for weekends and it is NEVER, EVER available. If you know you want to stay there (it is one of a handful of hotels in the Lincoln Park/Northalsted area) you would be wise to book a multi-day stay nine months to a year in advance. (No, I'm not kidding.)