Found a 91 Heritage Softail Classic with 45k miles. Will need some gaskets in near future but other than that in good shape. I keep reading about the case issues. However, I like this particular bike and the history behind it. Any advice?

 

If ya like it... buy it..
if the cases were a problem... they would have shown that by Now.. A friend has a '91 that makes an honest 100HP... stock '91 cases..
and not babied...

 

My '93 Heritage Classic has 71,000 miles on it, 45,000 of which I put on. Only gaskets or seals I've had to replace due to leaks were on the inner primary. Only major engine work done was replacement of the cam bearings and push rods. Not because it needed it but because I was in there replacing the cam so I figured what the hell.
Just remember to warm it up good for a few minutes before taking off. If you're one of these push the button and take off like a rocket guys you'll be having to change your base gaskets before you know it. I haven't heard about any problems with the cases.

 

Replace the lifters and upgrade the transmission sprocket hardware, two known weak points on pre-95 models.