Yes that includes your putter. Are you sure it is a putter spot and not an umbrella spot?

Yup... And so does a ball retreiver!

Yes, it does include the putter. The clip is for use while on the course for ease of getting at the putter. I had one of those and the clip works well and saves sliding the club in and out all the time

14 clubs max or you get a penalty . My cart bag has a 14 way divided top and a putter tube. I keep all 14 clubs in the divided section with the cover on the bag to transport it to and from the course but, when I put the bag on the cart and take the cover off I move the putter to the putter tube so it is easier to get to.

Joe,

There are NO silly questions. You're fine.

Yes, the 14 club rule includes the putter. Whether or not people choose to follow that RULE is up to them. I personally would never trust a "clip" to hold my putter, so, if I had a 14 slot/club, bag, I'd choose one of those slots to put my putter in. Some people may not want to use the clip. Like, there's a few guys at my club who have Staff bags with clips on them, because that's just what they prefer. Whatever you're most comfortable with, go for it.

Hi, Joey you could have 14 putters if you want (not the best though as you will need lofted clubs to negotiate deep bunkers)

Prehaps the clip on the side is for a ball retriever or a brolly. 

Cheers

Karl