I agree with the other posters pretty much. The upfront cost for supplies will depend on what you have on hand. I had some of the items that were needed, but after making my first gimmick decided to go ahead and buy all new supplies because some of the items I already owned weren't ideal and buying a new one would make it easier for making more gimmicks down the line (without giving anything away, I decided that having something made of metal rather than wood was worth the $1.99).
Your time to make your first gimmick will vary. Chris estimates 45 minutes to an hour on the DVD and that is probably about right. I made mine in about 35 minutes, but I think that was mostly due to the fact that I had already watched the instructional portion of the dvd a couple of times and was therefore able to fast forward through some sections. I made a couple more as soon as I was done and finished them both in less than 15 minutes.
The DVD is WELL worth purchasing. Not only does it do a great job of covering the angles and general essentials of performance, but the section on constructing the gimmick is so well done that my mother could follow it. It's thorough, well-explained, and takes it nice and slow so you never feel like he's moving too fast and you're missing something. Excellent, excellent, excellent instruction.
The only point where I would disagree with the others is on the time from construction to performance. I know everyone learns at a different pace and (more importantly) everyone has a different level of mastery at which they feel comfortable performing an effect (not to mention a different definition of 'mastery'). Five months seems like a lot to me for this effect. I'm not insulting Lupo in any way, it's just that my experience was different. If he feels like it took five months for him to feel comfortable performing it, that's his business and I'll bet he does a flawless job with it. For myself, I worked on it for an hour or two a day for about a week before I took it to my tester (a coworker that I use post-mirror phase to help me work out the rest of the kinks). He and I rolled it around for a day and then I went back and worked on it for another few days before I was ready to perform for others. So far, no detections and the gimmick has worked perfectly.
So, to wrap up this much longer than needed post. First, definitely buy the DVD. As far as learning time goes, it's going to pretty much be like any trick. It will depend on your personal comfort level of when you feel like you have a trick down and how much time you put in to get to that point.
Good luck! Come back and let us know how it went.