I have a Kenwood TS-440S with the Auto Tuner. It is my first HF rig and I love it. I picked it up from KA1RXB Sandy for a very fair price. I haven’t had to do much work on it. I did have the tuning knob freeze up on me but the TS-440 Yahoo group came to the rescue with instructions on how to free it up. A little bit of PB Blaster and some elbow grease to work it into the pot freed it up nicely. The radio isn’t hard to operate and hears very well.
I have a handful of contacts on SSB but my comfort zone is on FT-8 and JT-65. I’ve also played around with PSK31 although the keyboard on my Mac is terrible for typing. I have a Windows machine ready to install in the shack but I haven’t gotten around to it yet. When I do I’m sure I’ll spend some more time working PSK31. FT-8 and JT-65 are great for chasing DX but I’d like to a bit more ragchewing with my keyboard rather than just exchanging grids and signal reports.
A lot of people go with signal link adapters. I decided to go the custom cable route instead. I did all the research to build my own, but when I added up all the parts I was looking at $35 and several hours of work. I decided to purchase the same type of cable I was going to make from XGGCOMMS (Kenwood Digimode-2). It is very well made, uses 600:600 ohm transformers for audio isolation and the PTT is also optically isolated and uses an FTDI USB adapter. The radio does not have CAT control unless you install two chips from the IC-10 option. I have these in my cart on ebay but haven’t pulled the trigger yet.
Overall I would say that the TS-440S is a great older rig. It’s treated me well and I plan to keep it in my shack for some time to come. I would love to add a newer rig to my shack as well, but for now the TS-440S keeps gets me out on HF like a champ.