Steve has some great points here, heed the advice that his experience provides.
One other thing I think is relevant to adding weight is negative reps. I love doing slow negatives for advanced moves that you don’t quite have the strength for. One arm chins, full range handstand push ups, etc. In this case, specifically weighted chin up negatives. Grab a weight that will allow you to do only like 2 or 3 reps, jump to the top, and slooooowwwwly lower yourself down to the bottom; I’m talking 5 seconds minimum, but ideally 10 or more. Really feel the tension as your muscles expand; imagine slowly drawing back a bow or a huge rubber band. Try to get like 8 or so reps in per set, for about 3 sets. Then, the next workout, go back to full chin ups only without weight and see if you’ve improved.
I wouldn’t suggest doing heavy negatives for more than one exercise in one workout, as it is extremely taxing on the central nervous system. Also, be extremely cautious when using this approach for dips, since the shoulder mobility requirements are higher to begin with.
And, as I usually recommend, I encourage you to round out this training with back bridge variations and one leg squats (pistols and/or shrimps). Once you can do 20 really clean dips and I’d say a solid 15 pull ups, you can start working on handstand push ups. In the meantime, simply try to get comfortable holding a handstand at a wall, and you may want to practice hand balancing with the elbow lever and frog stand.
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