>>7
I have made some more progress over the last few days. I know for certain this will work; I have experience with hosting tor imageboards. Here is a screenshot of some test posts of the file uploading code.
I think, too, that getting a userbase is going to be a rather finicky and difficult. I have seen some posts by hapas on 4chan /r9k/, but I am unable to post there because 4chan is blocked in my country and I am only able to access it through VPNs.
I find it important to have two or three people who all the website code, keys, data and stuff is shared with - in the event of me not being willing or able to continue hosting, others can take up the torch. Mewch, 8ch.pl, 8ch.net etc. shutting down is good indication that such a redundancy measure is required.