Fudgie,
I have the 12" (Chrome) standard 444's - exactly what you are considering. Given what I considered the rough-ass ride on my '97 Tourer with the OEM shocks/springs I went Progressive on both at around 55K.
I'm 5'10" 180 lbs and would have welcomed any lowering of the bike this changeover provided. I ride solo 100% of the time.
Got to say - the rear rides better but I honestly feel the Progressive front springs did nothing to smooth out that aspect of the ride. I have the 444s set soft as possible and I do not change the setting even when I load her with 30-40 pounds of this and that when on road trips.
My advice for you would be to utilize the Progressive guidelines for shock selection - standard vs HD. Ignore the part that says there are no 444s that fit the Valk. Obviously, that ain't so...
While it looks like you might have a customer for your HDs I'm really not sure the stardards will give you the softness you want AND still tighten up enough when you travel two-up w/luggage.
This is a long post to say "Ask someone else", but being one who has wondered if the money spent on my springs/shocks package was worth it I'm not at all sure you're going to get all you want here...
Where are the guidelines on progressives page? Cant find them.
It seems my oem I/S shocks were shorter or maybe just softer and I could reach the ground better. I'm 5'-7" 210 and shes 5'-1" and 125 ish. I've been happy with the HD's in the 4,000 miles the last month or so. Just didn't want over kill. Thx!