On a large and/or elderly female, it's almost always best to take a second person into the room who can hold the flashlight and help keep the legs open. Also, I'll bring in an extra catheter just in case the first one ends up in the vagina (happens a lot!) and leave the cath there so I'll know where NOT to go on the second attempt.
In addition, sometimes I'll approach a difficult catheterization from the rear, with the patient lying on her side. This helps in cases where the woman has contractures of the lower extremities or hip pain; it was the only way I could get a catheter in one patient I had with MS.
The biggest challenge I've ever dealt with in this area, however, has to be the 650-pound lady with a chronic indwelling catheter which had to be changed every month. She couldn't lie flat for more than a few minutes; she couldn't get onto her side. Home health wouldn't touch her; nursing homes wouldn't take her.
So she came to the hospital once a month for catheter changes, and over time we developed a system. It took eight staff members to do it quickly and efficiently: one to hold the flashlight and lower the head of the bed, one on each side to keep her labia separated, three to hold up her enormous belly, one to take the old cath out, and one to put the new one in at the same time. We could usually get it done before she panicked and started screaming; we always got it done within five minutes of getting her prepped and lowering the HOB.
Ahhhhh........teamwork at its finest.