Hello
I live in Rugby so hopefully I can help you.
There are 4 high schools in Rugby which vary greatly. There are also 2 Grammar schools which are great but are extremely hard to get into.
The Rugby area varies a lot! Money will play a large part in the type of area you live in. Perrsonally I wouldn't live in Overslade, Brownsover or the area around what was the cattle market, (this is currently undergoing a regeneration programme)
I would live in Cawston, Bilton, Clifton and Dunchurch (this is really a village just outside Rugby) Woodlands is also nice.
WRT leisure time, we have Draycote Water just outside Rugby which is great for walking and just relaxing. There are the ususal cinema, bowling alley things for the teens but we don't have much beyond that. There is a skate-park by the sports centre.
We don't have a good range of shops in the town. For shopping I tend to go to Leamington Spa or Birmingham, Both easily accesible by train or bus. The normal weekly shop is catered for, supermarkets here are Tesco, Sainsburys and Asda.
Properties to buy, most of Rugby is older properties, turn of the century type thing. We have a lot of 1930's semis all over town. There has been an explosion of new builds over the last 10 years so there are loads of these around but it all depends on the area you are most interested in.
Personally I wouldn't buy an ex-local authority house unless the area had largely being sold off, I don't have a problem with council housing, they are all very well-built. But the areas tend to be very mixed between private and council, you don't always end up with the best area that way.
Hope that helps, if I can help with anything else, just let me know.