I'm 56 and I've never done the typical bar band cover song deal. In my 20s, to be honest I probably wasn't good enough to cut it. By the time my 30s and 40s rolled around, my chops were a lot better but I had a career and a good day job, and it just didn't appeal to me to do that.
What I did do was play in a bluegrass band for 10-15 yrs, either as a guitarist or bassist and had a pretty good time doing it. I'd still be doing it if the right opportunity presented itself. We played the occasional bar, but it was either our home hangout (paid decent) or a low key place in Birmingham or Atlanta that catered to the acoustic crowd. Our bread and butter was festivals and private parties. Festivals can be a drag too. Try playing 3 45 min sets in some city park on the back of some trailer in the blistering summer heat to fat women in flip flops and rug rats. Then tear down the PA. But we played some great ones too. Almost all of the bigger bluegrass festivals in the Southeast. The big festivals always provided sound. Show up, tune, look good, and play your best and you are always appreciated. Private parties were the best. We made $50-$100 man, got free food and beer, and a lot of the time didnt even have to set up a PA, just find a corner and jam, or just bring a little system at most.
Upon retirement, I've hooked up with a young 20 something singer songwriter. I'm playing upright, and we now have a full band that includes elec guitar and drums. Everyone is 20-30 yrs old cept me, I'm the old man. Its 80% original music, and 20% covers that we select. We've just completed a demo and are beginning to shop it around. Places within a 1-4 hr drive of North Alabama catering to original Americana-ish music are few and far between but there are a few. Plus there's the festival thing. We have no illusions of this being profitable. We're doing it because we love it.
If we can make the gas money we will go. And yes, there will be some obnoxious people and sloppy drunks to deal with, but hopefully not too many.