I went with my wife, another family (no kids), and 2 more guys. Stayed in 1 room with ac they asked for 3600 but we bargained for 2800 for 2 days.
Boarded train at 10 approximately but don't remember the exact time. It was sleeper class which is good in October end as it is an overnight journey and don't have to waste on ac. Well again depends on personal choice.
Train was on time. Food, chain and rest served by railway is as usual pathetic. So always better to carry snacks or cakes.
Got down in Pune.
Book ola or any cab but refrain from letting them come to the front gate of the station or the auto stand people will ask for pouti or hafta :) So tell the driver to come to a place where they won't reach the cab. Dont take autos in Pune, they will rip you off for sure.
Next day took zoom car from Pune. 5k for 360 km and 5k deposit. You should have a valid license with no cases against you or they won't give car and no alcohol (if found, or smell as well you will never get zoom car).
Matheran : try to avoid Sat, Sun or you will be in a crowded place with prices higher that expected. Try to start on Sat and reach there by Monday evening and book from evening and stay for 2 days or as per your budget.