Both directions, any size, no USB stick and no cloud account.
KEIBIDROP runs on both a Mac and a Windows PC and connects the two directly. Install it on both, connect once with a switch on the same Wi-Fi or a code across the internet, then drop files in either direction. With the one-time driver the Windows PC's files show up as a folder on the Mac and the Mac's files as a drive letter on Windows.
Install on the Mac: download, drag to Applications, open. Install on the PC: download, Extract all, open keibidrop.exe.
Connect once. Same Wi-Fi: the switch on both, then Connect. Anywhere else: Copy my code, send it in any chat, paste theirs, both press Connect.
Drop a file onto the window on either side. The other side presses Save. See it.
After the first connection the app offers their files as a folder. On the Mac it takes you to macFUSE, on Windows to WinFsp, one install each. Then the PC's files open in Finder and the Mac's files sit under a drive letter in Explorer, and a big video plays right away without a download. See it.
Yes. Names, folder structure and sizes arrive as they are. Timestamps are kept when you turn on Keep original timestamps in Settings.
Yes. Either side drops a file in and the other side saves it. The connection is the same in both directions.