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With regard to hamsters dying of the things you asked about with diabetes you will see the symptoms before it becomes a life threatening condition & they will need special care with diet, there isn't a lot more that you can do but it does involve regular testing of urine & making changes depending on the results, some can go on for quite a long time & live comfortably others will die more quickly & for some quality of life can become so poor they may need to be PTS, other conditions may not be so easy to diagnose although .certain symptoms or behaviours will often indicate a certain condition & others can be diagnosed by your vet, hamsters generally slow down a lot as they age whether sick or not, eating habits may change & some will just go to sleep & not wake when it's their time others aren't so lucky, as with any animal you have to judge quality of life, pain, distress etc & act accordingly.

As far as play dates go you have been lucky so far but as hamsters mature even those that seem to get on well they can suddenly fall out & fight, this can happen at any time really, it's not natural for hams to be together anyway, they don't need each others company so it's better to be safe than sorry & keep them apart at all times, fights can result in serious injury or worse so better for your hams not to risk that situation arising.