I personally think it depends on what you want to carry on you at all times and the level of detail.

1. The thumb drive is a great idea to save all your information and you can create different folders on how you want to be able to easily access your items but the downfall may be depending on someone if you do not have a laptop of tablet for easy access.

2. Drop box is great as well because you can access it anywhere there is an internet connection and do not need to carry anything around with you but the downfall here is that you need internet access and hopefully the device you are using has access to dropbox.

3. The Collector Assistant is also great because how much more information you can put with the item that a scan may not show as easily. What I do is just make PDF's when I update my collection and that can be carried with you on about any electric device or with the previous options given. Also, there is so much more freedom of how you can create different layouts as well so you can make a PDF for the entire collection of just pick and choose a few items.

When it comes down to it, there really is no bad way, it just depends on the situation. I personally have not had a chance to go to a chip show where it seems all of these options are available and left to local antique stores and coin shows where I like to just use my phone most of the times.

To answer your other question about being a beginner collector, I do not think there is a cut and dry answer. You say that you have over 5000 chips and that is by far more than what I have so I may say that you are not a beginner, but for someone that collects racks at a time that may be a starting point. It really comes down to if you are enjoying what you are collecting and wanting to add to it. I get a little bit of joy each time I get a new chip and hope that feeling never goes away.