Strings are a matter of what sound you like and there are a zillion choices.
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Your fingers will thank you for some light gauge. Light's are easier on your fingers.
Amazon.com: extra light bass strings: Musical Instruments Something in the $20 range will be fine for a year or so.
Yes that teacher will save you a lot of time. How much do you thing?
A LOT. Two months or 8 lessons will get you going. Most instructors will load you down with stuff - eight weeks in you will need to take a break, catch up and go over all you've been given. After you catch up go back for some more.
Welcome to the bottom end,