Over the years I've dealt with this situation more than once.
Here's some pointers.
The gun has to be powerful enough to positively do the job and one the user can handle.
That means if there's problems with strength in the hands or arms you have to balance the gun chosen with that fact.
This may mean the gun will be one that's not the best caliber for the job.
The gun has to be fairly small and easy to conceal.
A larger, heavier gun WILL get left at home sooner or later if it's too big or too heavy.
What constitutes "too big or too heavy" varies from person to person.
Generally, most any of the 2" to 3" barreled S&W "J" or "K" frame guns is perfect, usually fitted with rubber grips.
Consider a hammerless gun or one with the hammer spur removed to prevent catching in the clothes or chair rigging.
In automatics, there are many choices in "mini-guns" like the Kahr Arms or small guns from S&W.
ALL THAT COUNTS in a gun is that it be reliable. Accuracy is totally a non-issue.
NEVER carry the gun attached to the chair.
The very first thing an attacker will do is dump the person out of the chair so he's an easier victim.
If the gun is attached to the chair and the person transfers to a car seat and loads the chair separately, an attacker will simply grab the chair and pull it away from the user.
In either case, the person is disarmed without the attacker even knowing he was armed.
The method of carry ON THE PERSON, depends on the person.
Some methods are cross-draw, shoulder holster, and a fanny pack.
The ankle carry is not a good method, even though is sounds good.
it sounds good because the gun is close to the hands, and you don't have to lift a leg or squat to get the gun.
It's no good because a person in a chair can't get the pants legs up very fast, even if they're baggy. The chair interferes with that.
A strong side is dangerously unusable. Again, the chair interferes with the draw because of the sides and the tight fit. You can't brush the clothing back out of the way and get your arm between the chair and the gun to grip the gun. Plus, the gun is totally inaccessible to the off-hand.
The shoulder holster is very good, BUT it's hard to put on and sooner or later the gun will be left at home because it's too much trouble to put on.
Non-handicapped people are prone to the same problem and do the "I'm just running down to the store" only to walk into an armed robbery with the gun at home on the dresser.
A cross-draw works very good.
It conceals well when sitting, the gun is easily accessible with either hand, and it's fast to draw. A variation of the cross-draw is a driving holster made for bodyguards who drive the car.
These are usually quick-detachable-quick attaching so the guard can switch carry positions fast. This quick on and off snap system is easy to use.
It's hard to beat a fanny pack.
You can carry everything you need from the gun and reload to a wallet, cell phone, keys, etc all in one package.
This actually makes it LESS likely the gun will get left at home, since you have to make the effort to remove it from the pack.
On a handicapped person a fanny pack is less noticeable. Sitting, a black pack blends in with all the nylon and metal of the chair, and people are used to seeing handicapped people wearing packs.
A fanny pack is FAST if you choose the right one.
Since most people sitting keep their hands in their laps, you're hands are literally right on the gun. All you have to do is lift the coat or open the pack with one hand while the other hand draws the gun. As the gun clears, the off hand goes to a two-hand grip.
The pack needs to be one in which the front of the pack opens. The types that are a tunnel you slip your hand in or require peeling open the side are too slow and more difficult to work sitting.
The pack needs to include an internal holster for the gun to prevent the gun from flipping out when the pack is ripped open.
A pack that allows positioning the gun in a more upright position is better than one that positions the gun horizontally. This allows a faster draw.
The pack has to use a rip cord opener. The packs that use a plastic buckle or a peel-open feature to open are simply too hard to "find" and grip for a fast draw.
Training and tactics is necessary, more so than anyone else.
Since the user can't effectively run or take cover, you have to learn a "stand your ground and shoot it out" technique.
The user MUST learn never to threaten or brandish the gun.
An ordinary user can get away with that.
A person in a wheelchair can be encircled and attacked from the rear if the attacker knows he's armed.
Bluntly, the attacker should find out the victim is armed when he sees the muzzle flash.
Try to avoid trouble and even try to talk your way out of it, but when it's time to shoot....SHOOT.
You owe nothing at all to someone who is getting physical with a person in a wheelchair.
Legally and morally shooting is acceptable due to the disparity of force doctrine.
This is something the user either fully understands and will carry out, or he shouldn't be armed.
Last, even though it's very difficult for anyone, the wheelchair user MUST be more aware of his surroundings. The Jeff Cooper "Color codes" are something you have to take to heart.
Criminals are often like sharks: They circle, looking the target over before attacking. You have to keep your head up and eyes open.
The wheelchair user has to just learn to live his life staying OUT of bad neighborhoods, bars, and risky situations most people don't have to worry about.
Most handicapped people want to be very independent and may have trouble remembering that it's just too dangerous to go some places.
A favorite store at noon is one thing, the same store at night may be quite another.