We started tailgating about 4 years ago. I got a pass at the golds lot, and that was a lot of fun. The first year was the hardest for us because it was difficult to plan on amounts of people, so we were buying food for 25 and having 5 show, or vise versa, we spent a lot of money for little reward. Also at that time we only tailgated a few games, early in the year, and as it got colder we went to Embassy, or if it was an early kick we hit the bars. We did it in Golds for two years or so, and really couldn't get it going. My brother's inlaw tailgated on 10th and New Hampshire, and we went in with them a few times towards the end of the second year. Now we have moved up there for good. They have a built in set of guys, and I can filter in and out (I travel a lot for work), but my brother goes there every game. Overall if you get a few reliable people it isn't much work. They do a theme every week then everyone brings something, and that works out really well. In fact it is almost hard to get rid of food as people dont want to be rude...
Tailgating is fun, although I do miss the bars from time to time, but the group we have is pretty nice and they are good at making their own fun, we took the love to the Gophers game last year and that was one of the best 'gates we ever did... Unless you know you can get at least 10 people who want to throw down week after week, and your wife/gf/sig other is understanding that your are going to behave like a fifth grader a few days a year, then go for it, other wise stick to the bars, or find one to hook up with for a year or so, then see if you want to start your own.