Is your boat stored on a trailer or in the water?
I went through the same decision process when we bought our R-27. Our boat lives on its trailer in a Pacific NW wooded area, so we needed to cover it primarily to keep it clean and dry. After looking at all of the options, we spent the thousands of dollars (about 2.5 of them) for a custom mooring cover, but used a tarp for a few months while the cover was being made. It's a huge expense but we've never regretted spending the money.
It takes me about 10 minutes to install or remove the cover by myself. The benefit over the tarp is that the cover is heavy and custom-cut, so it's easier to handle in significant wind. It doesn't blow off while I'm getting it over the boat (the folding/unfolding process all takes place on top of the boat) and the entire cover is secured using six webbing straps at the stern that take about 60 seconds to buckle up. The whole process is pretty painless and I do it every time we use the boat (which is year-round).
The down-side is the cover is heavy, so it could be a challenge for some to hoist it up onto the top of the boat. I've not weighed ours but my best guess is it's around 40-50 pounds. It also gets pretty stiff and harder to fold when the temps are below 40. If you don't need the cover to be waterproof, using lighter material may solve those issues.
Bottom line for us, after using both tarps and a custom cover, we wouldn't hesitate to pay for the cover again.