I usually find if a razor isn't going to shave due to poor honing, it'll be pretty immediate. Either the first shave will be bad, or the second terrible.

I had this issue myself, I could put a pretty decent edge on a razor, but I was screwing it all up with my stropping. I'd say you're probably in need of stropping practice.

For me it was primarily a pressure issue. Too much tension on the strop, too much pressure on the blade. Loosening the tension a bit and letting the weight of the blade do the work, like with every other phase, seemed to get me where I wanted to be. You'll find your edges lasting longer and longer as you tune your technique. I started getting 5-10 shaves before needing to re-hone, then upwards of a month. Right now I'd say my edges probably last 2 or 3 months on just linen and leather.

The only negative from honing so often is wear on the blade. Every time you use a hone metal is being removed. So the longer you can keep it tuned with a strop, the better off you are.