How many watts does this system pump out and is it loud?

Don't know about the watts, but it has a very good power. Sounds low for a 50 people room. Hope it helps. Battery lasts enough. I bought 2 and put them together

What is the difference between the classic and first generation models?

Classic's doesn't has bluetooth and first generation has many feature, The Pyle PWMA1080iBT provides portable and wireless PA loudspeaker mobile entertainment. This versatile system was designed with quick audio setup in mind. Bluetooth streaming ability and built-in rechargeable battery give you wireless freedom, while the telescoping handle and rolling caster wheels allow for quick transport. Stream music from all of your favorite devices (like an iPhone, Android, Smartphone, iPad, Tablet, Computer, etc.). Use the included wireless microphone with the high-powered speaker system to control the crowd -- which makes it perfect for on-stage events, concerts or school auditoriums. Your message, or music, will be heard loud and clear thanks to the full-range stereo sound system, including subwoofer, mid-range and tweeter speakers. Additional 1/4'' microphone inputs allow for multiple people to communicate through the system, along with additional guitar / instrument input support for musical performances. Additional features include 30-pin iPod dock connector, ported enclosure for increased bass response, adjustable sound configuration controls, 35mm universal speaker stand mount, external 12V power input and more! Enjoy hours of wireless PA speaker performance with the Pyle PWMA1080iBT Bluetooth Speaker System.

Pyle Wireless Portable PA Speaker System - 800W Bluetooth Compatible Rechargeable Battery Powered Outdoor Sound Speaker Microphone Set w/ 30-Pin iPod dock, Wheels - 1/4" to AUX RCA Cable - PWMA1080IBT

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