The roof of my car is pushed in from people going on the roof. I got a few estimates on it, the cheapest being $2200!! I was wondering if I could push it back in place from the inside, and if by doing so would it increase the cost of the repair if I somehow screwed up?

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use a hammer
Bang formed inside! Use a hammer in the first response.
Depending on the car you might be able to push from the inside with ease. Do not use a hammer unless you know what you do because it will change the damage, usually for the worst. Much of the cost is headlining as the car passed it difficult to enter and is soft and can be a fair amount of costs.
use your feet and lay back to town and go on the roof.
selling cheap tooth extraction under $ 10 in hardware stores as Harbor Freight tools. I had one for less than $ 3 on sale. It is made of plastic and rubber. Simply place it on the centrality of the cutter and push extractor Dent flat on the surface and pull the lever clip in one direction and have their teeth and pull. The tooth must come out. Probably will save you money. Go out and try. If for some reason you can not get their hands on an extractor of teeth. You can try using a hairdryer and blow in the region of the tooth about 45 seconds to warm. Then place a bottle of compressed air down and give the area a tooth spray coverage. Then just wait about a minute and must leave Dent. However, this does not work all the time. The thinner the better metal works. Dent Extractor works better because it is stronger and has no chance of running all surfaces. I never had problems with the technique of compressing the air in the finishing of my car but every car is different. Therefore, use at your own risk. Should be very sure though. Either is better than paying $ 2,200. They would be delighted to receive $ 500 from me $ 300 would be reasonable. Good luck.
pushing the roof back up will not increase the cost to repair because the roof panel will have to be replace