I just bought a '14 enfield thunderbird (10k km) for 97k irp from a second hand dealer on bell street. It's scam city down there for enfield but there are a few decent bikes with neg. prices and plenty of other reliable hondas etc. Your other option is finding a secondhander on olx.in but it involves alot of legwork in the hectic chennai traffic.
Cant help with renting although for any period over a month buying and reselling has to be the economical choice - enfields (unless dropped/smashed) seem to hold their value pretty well.
Happy hunting!
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