A common workaround on the HOA thing that I've seen is just to put the antenna on the back of the house so it doesn't 'stick out' when viewed from the street. Makes the FCC vs CC&R argument a little easier to finesse.

The '20-40 mile' issue is the same as it's always been - how much do you want to spend for an antenna to get a clear signal? Community antenna systems (aka primordial cable) in rural areas often were set up with big antennae on a ridgetop for homes in a canyon, and got good signal (because of the good antennae) even 50-60 miles away from transmitters. A bigger problem might be direction: if you want to watch channels that are on different towers more than 5 or maybe 10 degrees apart, you will need a rotator because a good antenna will be quite directional. Again, nothing new about that for digital - has always been needed if you're using an outdoor-type antenna. Antennaweb shows where the transmitters are so you can tell whether you need a rotator.

Caveat though - as in the olde dayze, if you plan to put up an outside antenna talk with a knowledgeable installer (if you can find one) about lightning protection and the like. There might even be a building permit requirement for a large or high installation in some areas, for good reason.

People switched to cable from antenna TV because in general they got more channels more reliably without having to buy and maintain that Beast in the Back Yard (or on the roof). Still true if you want more than local TV, though digital does also provide subchannels, which our local crew makes extensive use of, giving you more viewing options than you might expect.

Then I get RRRadio & Hulu & Netflix & Youtube on the web and who cares...