A VPN would not cover up the fact that you used Tor at all. Assuming you're actually utilizing SSH through sock proxies and using a VPN, you can still be fingerprinted and tracked. There are already existing databases that have established profiles for various sites. Your ISP can easily see if you're connecting to one of those sites based on the type of data you're sending. Regardless if it's encrypted.
On the other hand, if you normally do this but forget to one time, it doesn't mean you're automatically exposed. It simply means that if anyone is currently attempting to find you and have an exploit that will actually work on you, then they will be getting you directly instead of your VPN. However, even if you had a VPN, if it's a government agency then generally speaking they will be able to find you anyways. A VPN doesn't "hide" you. It's not meant to.
If you want to stay anonymous, there are several methods that can be utilized. The most obvious one is not connecting to the internet from your own home. Use the Starbucks WiFi. A more clever method would be buying slave bots and using poorly secured wifi netowrks around them to hop over one. Assume VPN connections are from companies based in countries not on friendly terms with yours. Like China/U.S.
User -> RandomWifi -> VPN/SSH -> Slave -> SecondSlave/WifiHop -> VPN/SSH 2.0 -> Tor -> Market
This is a very basic set up. I would personally add more to it with other stuff, but it all depends on your threat model.
Small note. This assumes you're actually setting up your VPNs, not buying some "VPN service." I saw you wrote about being careful with VPNs and how "trustworthy" they are. I'm not sure why you would ever use a VPN service.
I'm exactly the same. Some favourites I've collected over the years:
3Blue1Brown - math essays
AlfieAesthetics - Bushcraft, botany and survival skills with some fun english humour mixed in
CNLohr - fun hardware hacking livestreams
Eliminator Performance - mechanical troubleshooting and maintenance vlogs
Engineering Explained - Automotive engineering explainers and mini-lectures
FearlessFront - Mechanical engineering, welding, and vehicle hacking
How to make everything - multi-skill projects on making things from scratch as much as possible
Kurzgesagt - Philosophy and science essays
Lie Likes Music - Music essays
Mathologer - Advanced (to me) Maths essays
Matthew Cremona - Woodworking
Matthias Wandel - Woodworking
Nativlang - Essays on the history of spoken and written language
Nerdwriter1 - Essays on Art, philosophy, and the sciences
Nightmare Masterclass - Essays on fringe culture
Numberphile - Mini-lectures on Maths
Polyphonic - Essays on Music
Primitive Technology - Vlogs on primative/ancient building techniques
Rick Beato (specifically his "What makes this song great" series) - Essays on what separates iconic music from the rest
Strange Parts - Hardware hacking projects, mainly based in Shenzhen, China
The Drug Classroom - Scientific essays on recreational drugs
This Exists - Essays on cultural oddities and internet culture specficially
Uri Tuchman - Very intricate woodworking and engraving
Wendover Productions - Video Essays on a variety of subjects including economics, travel, geography
Wisecrack - Essays which examine pop culture through a philosophical lens.
On the other hand, if you normally do this but forget to one time, it doesn't mean you're automatically exposed. It simply means that if anyone is currently attempting to find you and have an exploit that will actually work on you, then they will be getting you directly instead of your VPN. However, even if you had a VPN, if it's a government agency then generally speaking they will be able to find you anyways. A VPN doesn't "hide" you. It's not meant to.
If you want to stay anonymous, there are several methods that can be utilized. The most obvious one is not connecting to the internet from your own home. Use the Starbucks WiFi. A more clever method would be buying slave bots and using poorly secured wifi netowrks around them to hop over one. Assume VPN connections are from companies based in countries not on friendly terms with yours. Like China/U.S.
This is a very basic set up. I would personally add more to it with other stuff, but it all depends on your threat model.Small note. This assumes you're actually setting up your VPNs, not buying some "VPN service." I saw you wrote about being careful with VPNs and how "trustworthy" they are. I'm not sure why you would ever use a VPN service.