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about 3 to 6 months
It'll take a while man you have to push yourself if you want results and after a while fifty pushups will be easy and you need to make sure to make it tough on your self and do more pushups as your body starts to adapt to the work. Thats he only way to see change is keeping it hard and tricking your body into change by tweaking the workload as you go. Just do pushups to failure for like three months and you will see a visible difference but if you want to get buff you have to focus on compound movements and get in the gym and start moving some weight four or five days a week.
No way of telling. Depends on what else you're doing and what your eating habits are.
Depends on speed.
It will take 100 weeks, or just short of 2 years.