Anyone ever modify the kickstand in such a way that it allows the bike to lean over more?
I did. Not by design though. The addition of Wilbers shock jacked up the bike a bit and the lean angle on the sidestand is noticeably more.
I'm not sure that is a really good thing though, since the more the bike leans, the more weight is transferred to the sidestand.
A couple of years ago I went on a ride to Minden NB to meet a 'lunchbunch' from the MTF forum. That night we rode into Kearney NB and a big summer storm hit. We took shelter in a Pizza Hut (what better place to ride out a storm). The wind was howling and I thought the bike would be blown over for sure. All of our bikes, V-Strom, Wings, etc. were on their sidestands and no one lost their bike. IMHO, a sidestand provides a much more stable support, as long as it's deployed properly as outlined by others.
I lost a previous bagger to a fallover many years ago, due to using the centerstand on unstable ground. I have never had a bike fall off the sidestand. Always be sure I leave in 1st gear pointing uphill whenever possible. I never use the engine shutoff switch, but like some others, I leave the bike in 1st gear and drop the sidestand, hold the front brake while mounting and dismounting and let loose to take up the gear lash before lowering the machine onto the stand.
About the only time I regularly use the centerstand is in the garage.
As far as Harley making a better 'jiffey stand', I had a friend who bought a brand new Harley about 20 years ago. He was very proud of the bike until one day while parked something broke on the stand, the bike fell over and the kickstand punched a hole in his crankcase. Now, how special is that. I guess that would qualify as a 'bad Harley day' :detect: