A lot of negatives about being "inseam challenged"...I for one took the route similar to Merlyn and Slapp...early in my metric riding days I have had my share near and actual tip overs...and one has to do what one has to do to ride in a comfort zone with their passenger safety in mind. The key here is to lower as much as possible without bottoming suspension under heavy bumps or dragging hard parts in deep turns (usually canted on and off ramp sweepers) under firm braking or loaded conditions (when testing do solo with static loaded bike, aggressively in a controlled environ).
A few things I learned going thru this multiple times...do the majority of the lowering by seat and handlebar changes first...then work to lower BOTH the rear and front, usually an 1" or so at both ends at a time. One advantage is the fact that we generally weigh less, and with co-rider, the suspension sacks down an additional inch lower, only less suspension travel means stiffer progressive, stiffer lever/spring loading is needed (single shock setups can change lever linkage as well as springs which made things easier on metrics).
The front fork oil should be changed first, slightly thicker fork oil (from 5W standard to 7.5W to start, and shorter progressive dual coil springs and RaceTech Gold Valving (if option is available) added next Outback go with what other riders of your model usually opt for, i.e. shorter but stiffer Progressive or AirShocks (if you can afford 'em).
Yes, as Glider says, lowering kits mean greater likelyhood of bottoming out and rough ride, with plenty of negatives, but the alternative is road rash or unhappy co-rider. So do your due dilligence when lowering your bike to find out if you have cornering clearance or suspension issues, have them sorted before going on that 500 mile shakedown tour. Self preservation and honest effort to calm your riding partner fears are number one...and trumps just about everything we do to share our love of two wheeled sports. You are sold on HD...you have to sell it to your significant other or it is just another hobby you do on your own!