OK, I will jump in here and let you know my thoughts.
I would buy a decent amp. I do not know your budget so I would find the one with the most power that you can afford. If it were me... I would get a Fishman Loudbox Performer, Loudbox 100, Loudbox mini in that order, depending on which one you can afford. The Loudbox Performer will cover small to medium sized rooms and you will like the sound. I would also get a decent DI box. I use the Fishman Aura Spectrum DI which is way more than you need and it is expensive ($320), the other extreme would be a Behringer ADI21 at around $40 bucks. Why do you need a DI.... connection issues, better sound at the amp or PA. I own both of them, both will do the job. A decent Microphone, the recommended Shure is good. The Amp is the way to go for now. The other amp recommendation in this thread are good. So go play through a few and see which one speaks to you.
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Brad
Too many guitars, not enough talent.....YET!
JUST THE ACOUSTICS-
2007 GA8e Taylor
2005 ESM-10e Fender Ensenada
2005 850t Carvin Cobalt
Lots and Lots and Lots of Solid body Electrics
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