Do they check for VPN?

[bananan]

I'm set up like this... It's not completely ideal, as I'd like to ultimately end my opsec with socks5 or socks5>RDP
My current setup is this:
Host>VPN>VM>TOR>VPN>RDP
the reason Tor is in there is because I'm using whonix and run a vpn within it that only routes trafic through regular browser not tor browser through the second vpn. That way I can have tor running and tunnel through vpn to RDP in the same VM.
Please tell me any considerations I should make