I wouldn't recommend machines - they don't work the smaller stabilizing muscles around joints. I would go for free weights but start very sloooowly and not try to be Arnie to show off in the gym by piling on big weight. Concentrate of proper form and technique on low weight before moving up. You will find if you do that your joints become much stronger and stable - could even fix your gimp shoulder (depends on the injury). If you need a spot, just ask someone in the gym to help out for a heavy set.
To start I would focus on a good all round work out 2-3 times a week, doing compound exercises but as I said before, not going all out Arnie until you are ready. A typical simple work out would look like:
Bench Press
Bent over Row
Shoulder press/military press
Squat/deadlift (whichever you prefer)
Incline chest fly ***May hurt your shoulder so be careful!***
Lateral raise
Pull ups
Dips
Some core/ab work - whatever work for you
Start with around 8 reps, 3 or 4 sets. Make sure you do a warm up on each exercise before adding the weight.
A couple of months doing this work out a couple of times a week would give you a good solid grounding in lifting and then you can start mixing it up a bit.
(*All the above is IMHO)
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