Also might be worth looking at newer cars - some of them have started to have air-operated handbrakes now (even in the low-end ones!) which just operate by a button on the dash. Some of these also have a thing VW calls 'Auto Hold' which stops you rolling back when you do a hill start, which can come in handy - it makes driving them much more like driving an automatic.
Or you could just get an automatic
Personally I find there's usually one 'correct' way for me to do each task when driving - if I change gear while twisted a bit then I really feel it. When I was learning to fail my HGV test I found it really hard to get into two of the gears until my instructor suggested I grip the gearstick slightly differently for those gears (elbow up in the air instead of pointing down) - this let my shoulder hold together so I could apply a bit more force.
If you have an OT could you get them to have a look at how you're doing things?