i['ll start off with what I feel are the hardest:
Aiwa S30
One of the first few machines. However, unlike the TPS-L2, this one is ridiculously overly complex mechanically. First, to access the belt, the whole thing needs to be completely disassembled. Then, to place in a new belt, you will have to do so while the mechanism is separated into two pieces, while ensuring that everything lines up. Not to mention the high number of screws. On the other hand, the TPS-L2's belt is easy to change and is easily accessible.
Walkman 7
First Auto reverse model. Not so bad until you rip the flex cable going to the secondary board. Fixing it was incredibly difficult. while the dual azimuth is innovative, it is somewhat difficult to set up, even with the service manual. (And you cannot connect it to a PC soundcard to use Osci.)
Jams in the servo mechanism can be hard to pin down. Not to mention the shrinking gears problem I had.
Random Early 90s Logic controlled Aiwas
Aside from the capacitor problem, most of these require boards to be desoldered. Most of my Aiwa service manuals are pretty crap with barely any disassembly instructions. Boards have fragile traces. Boards corroded by leaky caps.
National/Panasonics with 2 rew/fwd buttons on the door
I only own one example in poor condition. Hey, a board that is completely made of the same stuff flexible cables are made with! Aiwa S-30 complexity! mine is beyond saving though (The flexible board has corroded beyond repair)
On the other hand, here is one of the easiest:
Sony EX/FX 1/equivalent machines based on same mechanism
Open the cover. Change the belt. No other adjustments required. done! One later model even uses pin based connection from the lower board to the top board- no desoldering!
What in your experience do you find are the most difficult?