My wife's maid-of-honor used to live by The Loop, drove down there many times. John Young Parkway has been pretty smooth since they opened the Sand Lake Road overpass, but Hunter's Creek/The Loop just keep growing.
Consider a 1-exit jump east on the 417 between John Young and 441 once you hit Hunter's Creek, which is rough. 441 is pretty desolate once you get south of Town Center Boulevard (around GatorLand/Tupperware).
Another relatively secret path is Orange Avenue, they've been widening it for a while now, and it's really wide around Meadow Woods, which is where they are proposing a SunRail/Brightline connecting station. You can jump over to I-4 on Michigan. And it won't be long before they open the connecting leg of Holden Avenue/Millennia Boulevard, which gives you another option for lateral movement.