Hire a WordPress Developer

I am looking to have a plugin or whatever you suggest to be made to help with the following: Be able to set different categories of files to go to Amazon S3 buckets. For example, theme files, wordpress core and other html or php files go to bucket1 and it will copy them over and change the location in code. Media such as jpegs, gifs go to bucket2. I would like to be able to turn that on or off. I would also like to be able to specify folders that would go over to Amazon S3 and have their locations be rewritten. I am having issues when I use Envira Gallery to add photos to the media gallery and the Add to Server plugin to add 98 photos to the media gallery. I get a 500 error with no errors in any of the logs that I can see. It is like it times out. My php times are set to 600. If I redo the publish it will continue for a while and do the same thing. I would like to be able to add photos to the server directly (since it is local) and bring them into the media gallery- if there is a better way to do it rather than the plugins on Wordpress already. I would like to be able to put a large video file on the server and have it transferred to another S3 bucket and then be setup in the elastic transcoder presets to come out as an adaptive streaming file. I want to be able to add the file to the post and have it play with whatever player is suggested. I want the best quality mp4 file to be linked to the post for download. This server is self hosted and located in my house. It is a Windows Server 2012 R2, 2.20 Ghz processors x2, 128 GB Ram, TBs of hard drive space. It is used as a blog to host our families photos, videos, daughters school work etc. Kind of like an archive. I want it to be made to last a while. I like the theme I found on Wordpress but if it can be made to do what I want I have no problem having it done from scratch. I know this will be a large job and the budget I set can be discussed. I want to be fair and also get a great job done with all of this. Thanks!