Hey Bobby,
TL:DR Version - When: When you stop seeing gains. Kegel: Yes. And take everything slowly and steadily.
The most basic answer to when you should switch up your routine is this:
When you stop seeing gains.
Essentially, if you get to a point where you're doing the basic routine as hard as you can and nothing's growing, then it might be time to switch it up.
That said, TYPICALLY I would say to do the basic routine for at least 5 - 6 months as it is not only just a solid routine, but it is one that aids in the conditioning (or reconditioning in my case) of the penis for harder workouts. In fact, I would tack on an extra few weeks just to make sure I'm not gaining anything else from it. DLD gained two inches, and a lot of people have gained as well, so don't worry about changing it up just yet.
Now, as much as I hate to admit it, you will inevitably have to switch up the routine once it's no longer working. You can do this in a combination three ways: More time, more power, or new exercises. Once the standard newb routine isn't working for you anymore, I would first advise you to add more time and power. Try doubling the stretch times, or jelqing more first. You'd be surprised how much more you can get out of the routine by just increasing the amount of time you spend stretching each day.
Okay, so now you've come to a block. You've stretched 36 hours a day for 10 days a week and somehow also jelqed 9000 times per day and you're doing it as hard as you can and nothing is growing. Now it's time to add some new stuff. Now your penis is probably so conditioned to basic stretching that you need new, powerful tools to make it grow. Now, (and I'd again recommend at least a few months of basic stretching/jelqing before adding new stuff) you can add a few of these (or others that you find) to the mix:
Slow Squash Jelqs, Clamping, Hanging, Bundled Stretches,
Power Assist Stretches, DLD Blasters, etc.
As for what to add first and how much, I'd say just start by adding one exercise for girth and one for length. Don't suddenly scrap the old routine and go into an all advanced exercise one. Take it slow, one by one, over time. This not only prevent injury, but also gives you a better idea of what's working. If you add say...Blasters to your routine, and suddenly you start gaining an inch a day, I'd say you PROBABLY wont need to tinker too much with that routine. Different things work for different people, and it takes time to try and see what works. As for how much to add of a certain exercise/technique, I'd say start slow and gradually add on more. As an example, if you're doing the Newb Routine and you want to add some bundled upward stretches, I'd say just start with 3 mins of that and add on more each week.
As for kegeling: Do it. It's part of the newb routine for a reason. Do it.
Hope this helps. I'm not a super mega ultra pro at Penis Enlargement, but I've been doing it for a while and this is the sum of my experiences.
Good luck!
