Contact The Mandolin Store. I followed their advice on either the Eastman 305 or 505. I got the 505 (a Xmas present from my wife). Go with A shape body, for the price range you want to stay in, you'll get more for your money.
For lessons, I am using the Peghead Nation beginner course as taught by Sharon Gilchrist. I did change the strings on my 505 from D'Addario to Thomastik Infeld and while I lost some volume (the TI's are lighter), I think the tone is as good or better. The lighter strings are certainly easier for learning proper fretting technique on the smaller neck. I have been very pleased how the combination of the TI strings on the 505 have resulted in an instrument that seems to stay in tune as well as my best guitars. That was a pleasant surprise given all the chatter about how hard mandolins are to keep in tune.
I was like you, wanted to expand my boundaries. I started 10 weeks ago and I'm having a lot of fun with it.
Good Luck!
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