My friend bought a gretsch streamliner g2622t guitar about 6 months ago and I was very impressed with the guitar, both build quality and the tones achievable with it, I was playing through a 50w Boss Katana amp when I tried it out and it really did sound great so that could be a something you may want to look into further.

As far as looper pedals go the Boss RC1 is the most simple looper to use on the market but it's also limited in its functions, having owned one myself before upgrading to the Boss RC3 I would definitely recommend the RC1 as a first looper pedal, really solid build quality and they hold their value really well too so if you do decide to upgrade at some point you'll still get a good price for it if you decide to sell it on eBay.