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At the bottom of your post you are submitting, select 'Manage Attachments'. In the new window that appears select 'Choose File'. Select your file then select 'Upload', the window will refresh and should show the name of the attached file. Then select 'Close Window'. When you submit your post, the pictures will be attached.
If you don't get the new window after clicking 'Manage Attachments' you need to check for a pop-up blocker in your browser. If you click 'Choose File' and upload a file and it isn't there, look in that same window for an error (maybe file size is too big).
You are correct. A benefit of being a paying member.
I have found no benefit for NOT buying a membership. One post should save you at lest the yearly fee (what is it now, $12?). Or you could not become a member and take your truck to a mechanic...it won't be cheaper than the yearly fee.