Maybe try yet another SFTP client (Filezilla and WinSCP share some code). For example Bitvise Tunnelier. Let us know the results.

So after more troubleshooting, if I completely disable the public Windows Firewall, WinSCP works fine. If I allow ports, or the program, or anything else there seems to be an issue with the transfer. Unfortunately, I don't know what the cause of that is, because I feel that allowing the ports should be enough.

I have tried all combinations of troubleshooting, even reinstalling Windows 8 on the laptop. For whatever reason, this Lenovo laptop has some odd issue with SFTP/SCP unless the public firewall is completely disabled.

Just wanted to bump to see if anyone had any other form of trouble shooting ideas?

Correct, Is there any better way to diagnose the problem?

EDIT:
I have already attempted a winsock reset, restore defaults on Firewall, I have attempted a reinstall of both network drivers (LAN, WLAN). Neither seem to really help or resolve my issue, and I have tried safe mode with networking.

Ok, so it's obviously something wrong with your system, not WinSCP (nor Filezilla).

Using FileZilla on the Windows 8.1 machine, I encounter the same issue.

This is pretty unfortunate. :/

EDIT: I just tested this on another machine (it runs linux) and I am able to transfer files perfectly fine using FileZilla.

Can you try any other SFTP/SCP client?

The Optimize Connection Buffer size is already disabled on my end when this is occurring.

If I enable the option, the same issue occurs.

Does it change anything, if you turn off Optimize connection buffer size?
https://winscp.net/eng/docs/ui_login_connection

I have no issues with Windows 8.1

I upgraded to Windows 8.1 yesterday and have been experiencing some issues that did not occur on Windows 8.0. I believe the issues are with the program itself (or Windows 8.1) versus the network in general. Prior to the 8.1 upgrade, I was able to transfer files without any issue. Now however, I am unable to get in more then a ~100 KB before it gives me the following errors (this occurs using sftp, or scp):

Network Error: Software caused connection abort
Copying files from remote side failed.


I have double checked my drivers, I have double checked the firewall and added a Rule in the Windows Advanced Firewall management for a program that would allow access.

However, no matter what I do, I am unable to transfer files.

Is this a common problem? I have been searching Google, but haven't come back with any conclusive hits. My laptop is as follows:
Lenovo Yoga 13
USB to Gigabit Ethernet Adapter

Network Topology Wise, I am behind a schools network.

Originally I was using the stable version of WinSCP, however, I upgraded to 5.2.4 (Build 3548) thinking that this would solve the problem, it did not. As mentioned above, this occurs on scp and sftp, I am using the Commander style interface,