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This may be a silly question, unless is isn't. Are you sure that your maximum upload speed is 300Mbps? Your maximum upload speed can be different to your maximum download speed. https://speedof.me can help you check.
If that's not the answer, sorry for possibly being overly simple, but some people might not realise.
Do you get better speeds transferring over Tailscale when both machines are on the same LAN? I have no problems pushing 400mbit over Tailscale but it does use a ton of CPU so maybe the Synology CPU is the bottleneck if you have similar speeds after eliminating your internet connection.
Have you tried using ZeroTier? I don‘t have much experience using Tailscale but have been using ZeroTier for two years now without any problems. Runs great on Synology
The tailscale guys are very responsive if you send them a question.. It's meant to be P2P but when it can't i believe it uses some kind of relay proxy server so at a guess i'd say it's that. Personally i run a subnet router on my LAN and not on individual devices.. maybe you could try that instead?
I’ve been trying to set up a subnet router, but can’t seem to be able to get the hang of it. Are there any good tutorials, or tips you could give me? (Sorry to bug you)
I have no experience with NAS but does it have an HDD? Maybe the read/write speed is the bottleneck. Again take this with a grain of salt since I do not have any experience with running a NAS.
HDD's can actually go a lil beyond 1000Mbps so that's not it :) And at home it does the job just fine