They don't call it a softtail for nothing.

 

20 year ago or not don't think you can't afford a touring bike, if you are looking at used bikes you will be surprised what you will find, and cheap.
Start shopping.
Good luck & Ride On.

 

Unless there's a pretty strange sissy bar on it now, it should be nothing to change. If you're using the original sideplates, you just take out a couple of screws or a few bolts if you're changing sideplates. Loads of sissy bars on Ebay.

To the OP - my softail has a pretty soft ride, but 2 big factors for your back are handlebars and seat (which are easy to replace, of course). You've ridden Japanese bikes, where there really aren't many after-market aprts available, compared to Harley. With a Harley, you can get pretty much anything you can imagine.

 

The issue is that virtually all motorcycles sold other than giant touring bikes are sprung for a single 170lb rider and come with lousy suspension components. Look on eBay and you can buy a pair of Sportster take-off shocks for $30-50. My sportster rides and handles fine - after spending $1,000 on suspension upgrades. But two-up accommodations and baggage aren't there.

Go with one of the bigger bikes, and get some aftermarket rear shocks built for your two-up weight. Front springs may or may not need replacement. You'll have a plush, well-controlled ride. Then find a good saddle. Used bike prices are so low right now (even in season) you can get something nice for not too many $$

 

really give it some thought as to how much you WILL ride, not want to ride, but how much time and money you got for actually ridein. so if you will only get to ride weekends and some durrin the week the harder ride of a softtail will be acceptable. but if you really will get to ride hundreds of miles a week for weeks at a time then the touring bikes cant be beat. and if your going to only do arround town and a couple hundred mile day once in a while the superglide is a good ride.
buy the bike to fit your ridein needs. I ride arround 20K a yr and the Ultra is one great bike for me. but it aint nothing for me to throw a leg over her and not get back home for 2 or 3 days, just cause I went for a ride.
AND if you got the experience you say then you will be ammazed how fast you pick up handlin the big bikes. and youll be amazed how good the big bikes can handle.. good luck man

 

I road from ElToro Calif to Baltimore on a KZ900 but that was 1976 . I had a Gold Wing in the 90s that I raod all the time and loved it. Very comfortable and handled like a much smaller bike. I doubt that I'll ride more than 5,000 mile a year and most will be less than 100 miles at a time. I'm thinking I could set up a road king or heritage for a soft ride. As much as I loved all the stuff, intercom, radio , windshield etc...I just don't have the $ to spend for an occasional ride. MAybe I'll change my mind as I'm pricing used bikes over the winter. I'm retiring in a month so I'll have the time to look

Thanks for all the input