Set up the same SFTP bookmark on both machines and run a test folder through Cyberduck before moving your whole workflow. Include hidden files, nested directories, a large file, and a file you plan to edit and upload again. That quick test will expose permission, overwrite, resume, and timestamp problems that a basic connection test misses.
Cyberduck is probably the most sensible starting point when you genuinely want the same client on macOS and Windows. Its interface is cleaner than FileZilla, but the lack of a permanent dual-pane layout can become annoying if you constantly compare local and remote folders. CrossFTP is closer to the traditional FileZilla workflow, though it feels less polished.
A detail people often overlook is bookmark and credential management. If you switch between two computers regularly, check whether you can reproduce your connection profiles without copying passwords around in a text file. Save the server’s SSH host-key fingerprint too. Otherwise, a warning after a server rebuild or DNS change is easy to dismiss without knowing whether the key actually should have changed.
I agree with @stackfox4658prime that SFTP matters more than changing the client’s appearance. Still, some “connection issues” are server-side limits, idle timeouts, passive-mode problems, or a host that closes too many simultaneous connections. If several clients fail in roughly the same place, replacing FileZilla will not solve that.
CloudMounter makes sense when you mostly open, rename, or edit individual remote files and want them visible in Finder or File Explorer. I would be cautious using any mounted-drive approach for large site deployments, thousands of small files, or anything where you need a clear transfer queue. The convenience can hide whether a file is cached locally, still uploading, or has failed.
If matching software on both platforms is mandatory, start with Cyberduck and try CrossFTP only if you miss the two-pane layout. If matching software is less important than getting the best tool on each OS, WinSCP on Windows and Transmit on Mac is the stronger setup. Keep the connection settings consistent and use SFTP keys on both.