I have never been an owner/operator of a 2nd Gen so no real clue what the differences are thru the years. I do know there are some things to look for when buying and if I were thinking of going that route I would want to know what they are. I never was an owner/operator of the 89 either but have swung the leg on the 83/85 MK1's a few times and gotta say if I were in your shoes and you like your 89 I would put a few hours of time in it and some cash to bring it up to road worthiness. I have criss crossed the country and most of Canada on our 83's numerous times and have always had great success with their reliability with very few failures thru the years. How many miles on your 89 @rpep1982? How many of those miles have you put on it and how long have you had it? I have no idea if yours has the 4 brush starter in it but all my 6 MK1's ran the 2 brush starter out to retirement of the bike and did that simply by taking the starter off when it started showing sign of doing what you mention and cleaning the carbon brush dust out and off the interior of the starter. One I actually did "feel" a looser armature bearing in and I replaced that. I also found that keeping a good battery in them helped with starter longevity as it keeps the starter from getting hot. If it were mine and it has the white, three wire stator terminal on the left side about 1/2 up the frame I would undo that terminal and ohm out the stator to see if the 3 legs match in resistance. If so I would use it as is and HARD WIRE that connection and do away with the terminal but thats only cause I had my fill of issues with that terminal early on in ownership. I would also drop in some Progressive springs in her forks if that hasnt been done. Doing so and you got a new bike right there! Are you sure on the shift shaft leak? Where are you seeing the leak? At the shift shaft under the cover where the shaft exits the internal block? There are numerous things that can cause oil to gather under there is why I ask. I would definitely take a look at the carb diaphrams too and make sure they are worthy no matter how many miles on it BUT, I would do the same thing if I sprung for a 2nd Gen or any other used bike that had CV carbs on it that I was going to trust with my kids in tow or even riding alone cross country. All that said, if you just want to ride something different than heck ya, I would opt for a 2nd Gen,, they are cool and definitely earned a reputation as 3rd place for the best of the best all time touring bikes BUT you already have the 2nd place title holder for that class with the 89.. 1st place still goes to the mighty 83/85 MK1 Puc