It might be useful if you can actually post your analysis, so we can know better about what we are talking about. It can also be useful if you can state the problem of interest, or hypothesis.
Meanwhile, in case the following general comments still make sense to you, I am trying a different way to see whether it can help you to understand the problem in your hands.
For Q1, here is an example using the Iris data among JMP sample data. This is a logistic regression of Species ~ Sepal Length. What the p-value that I highlighted in the screenshot means: Sepal can tell there are differences among three categories. But that is it, nothing else.
Further down the report, there is this estimates report. The p-values here indicate that setosa-vs-virginica and versicolor-vs-virginica are separable. But that is it, nothing more. No orders.
For Q2, I am not sure which report that you refer to. Following is a screenshot of "All Pairs, Tukey's HSD"
To interpret this report, you may want to check out this documentation: All Pairwise Comparisons This documentation is under Standard Least Squares platform, but the results are equivalent to what are in Fit Y by X.(numbers might be different by signs, due to ordering difference.)
Please read the first paragraph of the documentation carefully. When you compare pair by pair, different statistics have different meanings. In particular, you should look for words like "pairwise" and "joint". This is related to multiple comparisons. And you may want to read this wiki page to understand why the words matter: Multiple comparisons problem