Question 1:
YES. No problem to connect multiple midi devices over USB to your computer. But it ist important to assign the right midi in/out options. Sound interface are used to produce sound, but you can link up midi devices via an old fashioned midi connector.
Question 2:
To simply record your sounds you can use AUDACITY. Ableton LIVE ist a fully featured DAW. If you have LIVE you donīt need anything else to produce, record and edit sounds.
Question 3:
YES, or you are a kind of Beethoven, who was producing his tracks deaf.
Good speakers or at least headphones are necessary to listen to your music in a clean and dry way. Producing music with bass amplified headphones will result in the lack of bass in your recordings. This will be dramatic, when this music is played on other speakers or headphones!
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