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Welcome to you also Lauren.  If I missed any one, sorry.  Come back often and join in the sometimes turbulent conversation.  Not really, as stated above, ask lots of questions.  You will get an answer for sure.  And feel free to answer some for yourself.

That's good that you have someone pushing you to come of age.  I do prefer old music to most new stuff.  I guess thats where I'll remain.

You don't need a reason, just some money to get that next great deal.  It's all relative.

I just pulled this off the first site I googled. 
A well-oiled rosewood fretboard is essential to protecting your guitar's neck and its overall value. If a fretboard becomes too dry it can cause warping and cracking. Protecting your guitar's fretboard can be accomplished with very little effort. Preventative maintenance is the best insurance for any instrument.

Metal picks are out for me too.  Even the fingerpicks.

Now what would you really do with that third thumb

Rover, I meant Roger.

Good for you and good for him.  I have a Fender acoustic sitting here for a long time waiting for someone in my life to get interested and I will do the same.

Its all over youtube

All is fair in love and guitar technique.  Of course it is alright to sub a chord if it sounds good to you.  Many of us often take the short cut to make it easier. You don't have to follow the rules to be a good guitarist.  I do the same as Jerome, I use a G7 or C7 instead of a G9 or C9.  They are close enough that no one will ever ask you why you do it because they won't notice.

Congrats on the dobro buddy.  I may have to get one some day.  They're cool