In order to acheive this type of selection on the product page you'll have to use an external module, TB does not support such selection type currently.
1. FO - Front Office (the customer facing side), BO - back office - where you live most of the time.
2. Here is my 'size' settings in the attribute, in the last settings you have to select 'dropdown' and if you configured the product to use this 'condition' attribute it will show. After you make the attribute itself you have to go in it and give it values (used, broken, in pieces, brand new in box, found it on the street, etc.)
3. The system shows all the images you uploaded, when customer selects a condition and it has associated images for it the system will show the first of those as the large image and the rest in the carousel under the large image. A link saying 'show all images' will appear that will do what it says.
4. I don't understand what you mean here. Attributes are designed to do just that - list items that have different combinations so the customer can choose from them. There is also 'features' - for properties that are not different in different product combinations but different between products.
Post a screen from your attribute settings, attribute value settings, your BO->Product->Combinations and your FO->Product page showing the product so we can troubleshoot. 😉