Just moved away after 7 years so this was a good chance to reflect. sorry for the incoming long post!
Garage I at UCF is my favorite curb in east Orlando. Spent hundreds of hours in there. super fun bump in there as well.
Stardust Video is my favorite coffee shop and overrall best place to lurk in the city in my unhumble opinion, grab a drink and an outside table and watch the scene unfold. also spent hundreds of hours here too, but usually just thinking about life and getting stoked. food surprisingly consistently great. employees can be icey but its part of the charm. also good for early drinks, they have a full bar. every day you will see a cross section of orlando's weirdest but also most interesting and unpretentious people of all ages (in the mornings, a couple of dudes well into their 70s are usually hanging). i moved into an apartment in that area just to be within skating distance from the 'dust. i miss it dearly.
as far as bars go, i really enjoyed dirty laundry and lil indies, the bars attached to Wills pub. Wills is sick too. I'll take those over any new trendy spot. Guesthouse is a good hang right up the street, although pretty trendy. Tanquerays downtown is so sick too, but downtown for me was always kinda too crazy, and bars off of Mills Ave (like Wills) are a little quieter.
My favorite beer spot in Orlando however is Nora's, bar none. I'll say no more. Tons of cool bars near to that off viriginia Dr, you can get totally tanked just starting at lake ivanhoe and walking down Virginia towards mills and stopping at bars on the way.
black bean deli is an absolute must. vegetarian platter was a weekly operation.
if you're into electronic music or hip hop, go say whats up to Cliff and Jeff down at Remix record shop off mills. best dollar bins in Central florida for that music.
plus saved orlando for me. Keith will make you feel welcome. best dude, best shop.
if you want to get stoked on what has been done in Orlando peep the dice of life crew: