the issue with the second rule is most likely that you have selected the option to include shipping in the tax.
If you include shipping in the tax, you cannot use taxable total in the shipping rule, this creates an endless loop where the tax is recalculated because shipping has changed, then the shipping has to be recalculated, because the tax has changed etc....
the one constant with the other rules is that you are testing for an item with an ID of 19
Create a new php page and add a new cart display manager to it. On the second page of the display manager wizard, you can select columns to include in the cart display, add the ID column. this way you can see what ID value is stored in the cart.
Send me a link to your store including this new cart page so i can test it.