Thanks for the information.
With so much detail you should be able to build a tree around the main DNA match and incorporate quite a few of the Shared Matches.
To me the 285 cM match may be a Half 1st Cousin Once Removed which would point towards the Grandfather spreading his seeds and this would be my starting presumption if I was faced with such a match.
If the tree does not support this I would then look back a Generation for the MRCA which means looking at a Sibling of the Grandfather?
The above does assume that the generational distances are once removed, perhaps I should have asked for clarification.
Another issue with DNA Matches in this cM range is that there are a lot of possible relationship options and it is a case of working through developing the tree.
If you do what you have been advised to do and use the WATO tool that will result in a numerical result and %age probabilities for the options which in turn will provide more guidance on where to concentrate ones endeavours.
Alas there is no easy way.
Now as for the Leeds Method, the idea is to allocate the matches to each Grandparental line, ideally one creates eight groups, one for each Great Grandparent and their descendants using the DNA matches in the 90 to 400 cM range, making sure that siblings and first Cousins are not included in the data, the results indicate the line where each of the matches are likely to have their MRCA with you.
Do read the text that goes with the description as there are limitations to be aware of.
You should now have enough advice on how to proceed.