Derek C. said:
is that the kind of thing that looks fine right up until it isn't
Derek, short answer: 1 hour 35 in a very large hub is doable but it has no slack in it, and I would not book it without doing three specific things first. I have made worse connections comfortably and missed easier ones, and the difference was never luck, it was whether the transfer had been logged properly.
First, the timing that actually matters to you is not the published minimum connection time, it is that you are boarded first and off last. Assume you are still on the aircraft 15 to 20 minutes after the doors open, longer if the ground crew are stretched or the aircraft is parked on a remote stand and you need a lift vehicle rather than a jetty. That is the chunk the booking engine knows nothing about.
Second, and this is Sue's point and it is the big one, assistance is arranged per airport, not per journey. You want it logged at departure, at the transfer airport, and at arrival, and the transfer entry is the one that goes missing. When you ring the airline, ask them to confirm assistance is loaded against all three, and ask what code they have put on your booking. The industry uses WCHR for someone who can walk short distances but needs a chair to the gate, WCHS for someone who cannot manage steps, and WCHC for someone who needs help right to the aircraft seat. If they have you down as WCHR and you actually need WCHC, the wrong sort of help turns up and you lose your buffer arguing about it. Request all of it at least 48 hours ahead, which is the standard notice period, and reconfirm at check in.
Third, decide what happens to your own chair at the transfer. On a connection you normally want your chair brought to the aircraft door at every stop rather than checked all the way through to the final destination, otherwise you spend the whole layover in an airport chair being pushed by a stranger. Say this explicitly at check in, because through-checking equipment is the default at some airlines. How that works, and why it matters for the chair itself, is in flying with a wheelchair, and the booking side of the assistance is in airport special assistance.
Neil is right about the single ticket and I would treat it as non negotiable on a tight connection. If it is one ticket and the transfer is properly logged, I would take 1 hour 35. If it is two tickets, or nobody will confirm the middle airport, I would pay for the direct and sleep at night.