How about renting one for a weekend trip?

Balloo

 

Adding a back rest can be fairly inexpensive.
I went from a Ultra to a Deluxe.

What kind of riding are you going to be doing most of the time (is the question I would ask myself)?

I have not been on any 2000-3000 miles trips on the softail yet, but once summer hits I will.
The one thing I may miss is the gel seat I had on the Ultra.
If I miss it to much I will add one, time will tell.
The back rest I added to my Deluxe works great.

 

Keep in mind, a Road Glide Ultra is 900 lbs.
So, compared to your Deluxe, riding that is going to
be like wrestling a fat woman that's built like a
refrigerator.

 

That is a great idear. I did exactly that last May in Hawaii. I have a Deluxe, and rented a Road King. I was really worried that I'd feel the need to sell the Deluxe and buy a new RK. Renting one cured me of that.

Yeah, it had more power than my bike, but the ride was quite a bit stiffer, and the overall feel was "unsatisfying."

So renting would be a good way to help you decide.

I use a back rest frequently. Sometimes a back brace too on "bad back days."

 

One thing to consider . Out have a bike now that only averaged 1 k a year. Has dropped 10 k in value. I got to ride one year put 20 k on my road glide ended up taking care of my parents for close to 3 years . Oly got to ride about 1500 miles in those 3 years. At least my bikes have always been payed for. Actually got to ride last year a little about 7 thousand miles .

 

Depending how your back is, is going to determine what you can do. The ultras are a great ride when set up properly, but they are heavy and tough to maneuver when stopped. Make sure your back/legs can support those type of things. I test rode the 18 heritage, fatboy, and last Friday the sportglide. The heritage was the most comfortable, with the fb and sg about tied. It all depends on what you want/need. I can tell you after testing the sport glide and then getting back on a 15 road glide, the roadie felt like a barge, lol. The new softies absorb bumps really well. Test ride a few, you may be surprised.

 

Deluxe is fairly easy to handle and can be comfortable with few mods on the other hands full dressers are beasts in the beginning and gets easier after putting 50K miles on them. If you are planning to ride same miles as the Deluxe then won't get the dresser it's going to be too much bike.

 

Was in the same boat you are in, 08 deluxe 7500 miles, with more time for the wife to ride, looked at adding a better seat, suspension, backrest, but we want to ride on weekends away, then would need bags, when would it stop. Went in to get a new rear tire and drove out with a 2018 Road glide special. I had never ridden a touring bike but its so much better in all aspects of what I wanted. It's smoother riding, handling, plenty of pep with the M8,( did do a stage 1), I got a decent trade in for the deluxe. Id say test ride a bike but be careful it will be addictive.

 

Once I started thinking about a new bike, I know it's a matter of time before I make the change. So, I wouldn't put any money into the old one, since you probably won't have it long.
Start shopping for that new bike, while Winter pricing is good.

 

A Grasshopper backrest is pretty cheap and found on EBay. If you don't like it they will take it back. Cheap enough to try and see it it does what you need it to.