On a visit north this summer, we spent an evening in the Lincoln Square neighborhood of Chicago. Lincoln Square has a very lively "Main Street"; the stores all stay open until 9, restaurants later.
Only a couple buildings were higher than 3 stories (one was a new library, another was the old library building now being used as a music center). And, the tree lined street felt very comfortable - pedestrian friendly for sure.
In the center of the Main St area was a small plaza area.
On a Wednesday evening the plaza was packed; the event was a fiddle contest. A steady stream of amateur fiddle players, sometimes accompanied by other musicians, each played for a couple minutes and were followed by another fiddler. Many people of all ages enjoyed the free entertainment. Diversity of age, ethnicity and economic levels being was apparent.
Apparently there are weekly evening events along with a number of weekend events.
This street is likely one of the model streets that urban designers study to see what makes a lively, pedestrian friendly street - it certainly was lively and pedestrian friendly when we visited.
This area seemed to have all the elements that Sarasota is seeking for our downtown. The 4-6 block area had a variety of retail, restaurants, bars, museum and library. A celebrated Louis Sullivan building graces the middle of a block.