Reg fee.
You can still hang reg great single words with the io domain. Shoess is not a great word and just looks a bit silly. Adding additional duplicate letters to words is generally not considered good, evidenced by the fact that sites like brandbucket etc won't touch them.
Org domains can do well in certain circumstances but again "the shoes" is unnatural and clunky and that kind of business really doesn't suit .org
The valuation tools you mentioned can be helpful, but don't treat them as gospel.