looks like no-one wants to reply to the question so let me....
I have a 2007 Street Bob.....
I purchased a pillion pad and because I only wanted occasional use so fitted the four (4) rubber blocks to the seat (following placement instructions for fender) and not the guard. No sooner had someone sat on the pad that it left marks in the paint from the staples used on the underside of the pad. Now, had I fitted the blocks to the guard it would have not made any difference as others with the 2007 did this and same result with damage to guard. I purchased some lambswool and cut to shape and fitted under the pad... problem solved.
Believe HD made minor changes so that the staples were not able to touch the fender at a later date.... by all meand fit the blocks/feet to the seat but look carefully for any pressure on the edge of the seat when someone sits to make sure the staples wont hit. So long as the blocks are in the right place it wont make any difference whether on seat or guard.
I hated the ride with the solo seat and purchased a Mustang solo with seperate pillion pad. The Mustang pillion pad has rubber stops fitted to the pad, but I also have a fender bib that I leave on the bike when fitting the pillion pad and no problems.
enjoy
the rubber pads can mark your paint work...you could put some soft cloth between the fender and the pads too not have any problems...muddy