My LE came with 19s and I run 18s as my winter tires, so hopefully I can shed some light on your issues.
First, let me start with your last question. It depends. If you aren't planning to use your 18s again, then you can transfer them. If you plan to reuse your 18s then no. The only way you could transfer the monitors is to unmount your tires to do the transfer. Not economical and not good for your tires if you do this more than once. If you're going to sell your 18s, they won't be worth substantially less because they don't have the monitors.
My LE did not come with PASM, so I'm not sure why it would be a requirement when equipped with 19s. The widths on my 19s are 8" frt and 9.5" rear. If you put 19" Contis on, you'll probably not notice much difference in performance or ride between the 2 sizes. Neb has never been accused of having billiard table smooth roads and I've never had a problem with bent rims. If you hit a hole big enough to bend a 19, chances are it would bend an 18 too.
Should you put 19s on your Box? Absolutely, they look good on a 987S. Others may talk about extra weight and extra unsprung weight, but it won't be that much of a factor in every day driving. Do it.
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GPRPCA Chief Driving Instructor
2008 Boxster S Limited Edition #005
2008 Cayman S Sport - Signal Green
1989 928 S4 5 spd - black
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