We had two Indian Royal Enfields which were both bought in New Delhi.
Barak bought his 2007 Royal Enfield Thunderbird from another traveler for 55,000 Indian rupees (or approximately 900 US dollars), the sprocket and chain needed to be changed but otherwise it was in good shape.
(Edit 2/13/15) At the end of the trip Barak sold his Enfield for 100,000 Nepali rupees ($1000 US) but offered to take off whatever cost for repairs included, after a new piston Barak got 80,000 rupees for the bike. So after buying in India and driving it for 6 months Barak spent around $100 for the bike and perhaps another $100-$200 in repairs or spares (things like new oil, flat tire, chain and sprocket as well as maintenance). At one point someone else crashed Barak’s bike and the head gasket had to be replaced as well as the piston rings, Barak was massively overcharged and it cost $300 but the person who crashed it had offered to pay so the cost was not included).
Raymond bought a 2012 Royal Enfield Bullet for 95,000 Indian rupees from Saraswati motors in Karol Bagh. The bike was in great shape however they promised to change the oil, filters and cables before giving it to him. Although they claimed they did this, a small amount of investigation showed they actually did nothing. However the Motorcycle is in great shape and has experienced any problems in over 3 months of use.
(edit 2/13/15) At the end of his trip Raymond sold his bike for 110,000 Nepali rupees, however it is important to note that Raymond had significantly less time to sell his bike then Barak and could probably have gotten a better price. Also Raymond’s bike had significantly less problems than Barak so while he spent marginally more, if one has the money to spare it may be in their best interest to buy a newer more expensive bike. After it was sold the new buyer paid around 10,000 Nepali rupees for repairs and maintenance, so their final cost was 120,000 Nepali rupees ($1,200 US)