Thanks for taking the time to discuss.
You missed one thing -
Silicone (At least the Monkey Snot), is consistent. Response will vary from pad to pad, but if you know the yo-yo, you can beef up the yoyo silicone a bit, or recess more. It does get kind of fussy 
Some yo-yo’s are an odd size, you take whatever pad is available, and it just might be slippy.
You raised a good point, a week or two of replacement is too much, but I tend to rotate my snotted yo-yos for this reason or at least plan to…
I’m new to silicone, at least doing it myself, but I have been yo-yoing long enough to know there is a substantial difference in play to the better. If I had to try to sum it, it’s the bind - snappy, but no snag during play.
PS - Try the Monkey Snot, it would be a good follow up. Maybe they’ll comp you 
I slowly use mine until all the silicone is gone and then have a day where I do them all at once. I have been using flowable silicone from auto zone forever, never bought pads. The only time it fails to last a long time for me is when I put to much and try to slowly grind it down and end up ripping the whole thing out. Curing is pretty important too, if you don’t cure it for the suggested time it can cause premature wear. Flowable rips to shreds easily and isn’t as durable as most the pads you get pre made.
How often do you need to replace pads?
It varies for me some depending on the pads, but I would say several months of constant play.
Unfortunately, I didn’t time it, but I had a topdeck I used as my EDC for I think a year straight, and replace the pads once.
Pads last a long time, the problem with getting solid data on it is the number of variables.
Most people don’t throw just one yoyo constantly for months on end 
I do want to try monkey snot some time 
Would your yoyo get damaged from not changing the pads?
No.
but you might.
Not really any way I can think of.
Unless you slip the bind and ding it or something.
Silicone is great to apply to large numbers of yoyos at once, but for me, its a big fuss to go through just to do one or two throws at a time. My collection is not anywhere near the size of a lot of people, and the endeavor of getting everything ready ends up preventing me from siliconing yoyos that need it for a long time.
The good and the bad about flowable silicone response.
-
The good> if you know how to prepare, apply and finish the flow applied rings; you will seldom encounter any kind of problems.
-
The bad> If you get a tube of flowable silicone and you don’t know what you are doing; then your troubles will arrive with a quickness.
Improper preparation and/or application techniques are responsible for most failures.
…
This. I have silicone in some yoyos from 2011. I know some people that have it from the early 2000s. It all depends.