Domain flipping tests

Hello.

I'm new to the online marketing world. I purchased 4 local sites that had expired hoping to flip them for $100 each. I tried 4 different types of businesses - a realty branded domain around a lake up north, a Dance studio, a Pediatrics office and a hair salon. Each are popular names that have several businesses with the same name across the US, so they should have appealed to several biz owners. Didn't have much luck in selling them though. One realtor agreed and then backed out claiming what I was doing was illegal. I was hoping to try to build up to flipping 10-15 a month to earn $1k a month. I'm doubting myself now as to whether this is feasible.

Next, I bought an expired domain that is related to comedy clubs in a major US city. The words "comedy club (the city name)" get about 2500 searches a month. There are 10-12comedy clubs in the city.

I was thinking of trying to flip it quickly. Now I'm leaning towards trying to develop it a bit to get it ranked near #1 on Google for those 3 words. I thought it would be a good learning experience, plus may be easier to flip later.

I'd appreciate some feedback on this plan and maybe some ideas on what might and might not work.

I know I need to produce some content to get ranked, how would recommend I do this - write about upcoming comedy shows in the city - sort of like a "Comedy shows for this weekend" type of info? Love to hear your ideas. Appreciate your help!