Will this plugin do what I need?

Hello,

Thanks for getting in touch with us.

1. I would like to charge by category quantity only, not just overall quantity. Will this plugin allow 2 rules in this use case? If cart category = Tshirts AND category quantity = 1 then charge 2.95? I would then create a second rule for category quantity being 2 or more, 5 or more so on and so forth. The reason is because we can use first class shipping for USPS with 1 shirt. 2 is pushing it on their 13oz/16oz restriction.

Solution: The use-cases you have mentioned that is possible with the premium version of the plugin.

Here we have implemented your case in our site. Please see the screenshots.

The additional quantity of specified product will add the additional price for that shipping method which we have defined.

Shipping method screenshot: https://prnt.sc/kdb6ze
The method applies on the front side: https://prnt.sc/kdb8f2

2. We also sell mesh wreaths. These are a flat cost to ship (and super rare when someone buys two). Can we use the above rule, in conjunction with another rule to charge flat rate per wreath and use the higher of the two?

Solution: Yes you can achieve by using master settings, where there are options to apply the highest or lowest shipping methods. Please see the screenshot of master settings.

Master Settings Screenshot: https://prnt.sc/kdb8y4

3. Pretty sure it can do this in the free version – but if cart total equals 100 get free shipping. Just make sure I understand that right

Solution: Yes, You can create a Free shipping method and set a rule like Cart Total: Equal to 100. It will work

Let us know if you have any other query.

Thank you,
Multidots