Expanding this outside of just the Cleveland radio topic where it was posted, I think there are many factors that play a part in whether stations do remote broadcasts - or as many as they used to. Smaller and medium market stations I would say don't do nearly as many. For one thing, auto dealerships, which were once staple clients for weekend remotes at least a few times per summer, have changed where and how they spend their ad dollars and at times the ad budget is no longer controlled by the local dealers themselves anymore. Many smaller businesses that would once do remotes to celebrate an event or a store opening simply don't have the ad $$ that they used to, as they have more and more competition from big box stores and internet commerce. As the cost of groceries goes up for all of us, so does the expenses for raw goods that restaurants, bars and eateries buy, and they need to strike a balance between still offering value vs. raising menu prices to offset their increased costs without losing too many customers in the process - and so they don't often have the funds to host remotes as they once did. Festivals, fairs, concerts and community events don't get as much live on-air exposure - for one thing stations don't have the engineers, board-ops and even live talent they once had to make themselves available to do remotes from those kinds of events (yes, I realize with modern tech and automation perhaps not all those people are required for the actual on-air part) and if they do, it costs $$ to do those live broadcasts and many stations, especially those in medium markets and smaller, are having a tough time financially.
A few things that made remotes work were, 1) A seeming endorsement of a business from a voice people knew and had formed a bond with by listening to them on the radio. 2) The ability to get to see those jocks or hosts in person and put a name to a face, maybe even get to chat with someone who was "local famous", and 3 ) Games and contests they could potentially win. For various reasons, most all these have gone away or have reduced importance or are now a bit of a throwback to a different time, though for many that "different time" may not seem that long ago.
I can share that, for us at least, the last handful of new restaurants we decided to try and at least a few entertainment events we've attended, we discovered because ads for them popped up in our Facebook or Instagram feeds or showed up in our e-mail inboxes after we'd attended past, similar events. We didn't hear them advertised on the radio...and in our case at least, the $$ those business spent advertising on social media worked.