$500 · Mac vs. PC: can you help?

I have an iphone 6s plus that has about 300 voice memos, (mostly vocal demos for music projects). When I download from iphone to itunes on my newish HP Envy desktop they get scrambled. They don't appear in the order that they appear on my phone. I have tried to adjust the viewing criteria. I also have a Macbook pro, from 2008, in El capitan. I am not that enthused with the mac universe but I would like to reconcile my files in a functional way as I prepare to learn how to edit audio and video to complete projects. -I'm not useless on these machines, but I have admit I'm encountering little shitty bottle-necks when it comes to organizing and backing up and protecting my precious files. I've been burned thusly, by both Mac and PC camps, losing data and patience in my effort handle these issues efficiently. -But we are talking about moving voice memos, photos and videos into a place where I can feel confident to: -Keep the files in the order as they appear on my portable devices (phones, simple voice memo recorders -- mostly) when transferring and backing them up on my PC and Mac. -Create simple, automatic back up protocols via external hard drives through time machine (mac) and dropbox and external hard drives on my PC... or whatever is better than that :) -If we can do that, I'll be happy. Eventually I'm going to aim to learn how to harvest and edit these files through editing software. Like iphoto, garage band, and eventually Ableton, Pro tools, and Photoshop, etc. -That's the goal, but first, meeting someone who can help me decipher this seemingly simple but oddly difficult media rendering would be great. I'm not looking to re-invent the wheel--I just need these files to be available and safe in a chronological order. I cannot afford a pro, but If you think you can help, I am willing to discuss reasonable wages, by the hour to get it done, for cash. I would be right there, working and learning as we go, so if you feel you can explain yourself as we go, that would be a plus. I'm also friendly and easy to get along with and we could meet in my lovely home. I don't need a long resume in your reply, but if you could explain your (reasonable) confidence in this field that might help me get back to you sooner. Thanks for checking!