As far as how long it would take to do something custom, that would be something that we could discuss privately, as I would need to get a lot more details on how you would want it to work, and figure out which other features of the plugin you would want duplicated for another role so that the settings could be independent, and which features could use the same settings for both of the new roles. Taxes enabled/disable, tax rates, tax display settings, shipping enabled/disabled, payment enabled/disabled, coupons enabled/disabled, wholesale messages, etc… right now those are all set to apply to the wholesale customer role. If there is another role added with its own price, then we have to decide if they get separate settings for all those other things as well.
If it’s only one additional price field for the additional role, and everything else stays the same, then I could probably get that code put together and tested in one solid day of work, since a lot of it will be copy and paste, but there will be additional logic required all over the place where prices are shown and totals calculated to determine which price should be used.
As far as the other pricing plugin that I’m currently in the middle of developing, it’s a small part of a very large and complex system we are putting together for the client, and much of what would be “options” is hard coded for the client, but I have already thought about breaking that out into its own plugin and making it more flexible with options/settings, to sell to the general public. Can’t say when that would be yet. Still working on that big project and hope it have it mostly wrapped up by the end of next week.