I've just had mine done but mine goes over the kitchen as well, its probably a days work for two guys including stripping back, are you worried about a guarantee, as mine is over the house I got a 3 layer Bauder system that gives a 20yr guarantee, you probaly won't need that, if your replacing the boards if you use chipboard and it leaks again it'll be ruined whereas T&G softwood or WBP ply would dry out again but will be a lot more money.
It depends on what quality you are prepared to pay for, the cheapest will be chipboard and one step above a shed felt that can be torched on but I wouldn't have that.
£500 would be too cheap, I'd think £1,000 for a simple system
Do you need fascias and soffits? you say the boarding if rotten have any of the joist ends rotted? all this will add cost