Sounds like you're coming into a plan - but just to throw this out there: I go to Disney often, 4-5 times a year, as I'm a reasonable 3 hour drive away - I do a mix of solo trips, trips with friends, and trips with larger groups...on my solo trips, and some trips with friends, my arrival day is usually catered around spending time at Disney Springs rather than bother with booking a park day. I don't arrive super-early, usually between noon and 3pm - so after checking in (and unpacking if my room is available), I head over to Disney Springs and enjoy a wide selection of bars, restaurants, live music and entertainment for the rest of the day/night. Sometimes if I arrive earlier, I'll go tour around a resort for a bit just for fun, then head to Disney Springs.
The resorts that are connected to Disney Springs are favorites when going solo for just this reason...my upcoming trip on the 2nd week of December will be at Saratoga Springs, requesting Congress Park section, so I can walk in and out of Disney Springs at will. If my room isn't ready, I walk over, grab a drink, listen to a musician play somewhere - then I get my text that the room is ready, so I walk back, unpack, then walk back to Disney Springs for dinner, more entertainment, cocktails, etc. And no worries about busses back at the end of the evening as my resort is a quick walk home. OKW and the Port Orleans resorts are also good for this, as they at least have the boats to Disney Springs.
There are so many places for live music at Disney Springs - Marketplace stage, Waterside stage, Dockside Margaritas, Paradiso 37, Edison, House of Blues, Raglan Road, Splitsville - plus other spots that play music, have DJs, etc.