Password Manager:
Like @kxkvi, I’ve been using Keepass every day for many years now and I’m a fan. Unlike other password managers (like Lastpass, which I have to use for work), Keepass stores all the data locally (and encrypted); there’s no cloud service provider, no third-party website to get hacked, or anything like that. You can sync it via dropbox or other file-sharing site if you want. But I just manually copy it to my phone, a backup drive, and a USB stick or two. I don’t use cloud sync for anything yet.
I think there are versions of it on every common OS - I use Windows and Android but I think when I used a Chromebook I had it there too and I know I could use it on the Mac if I wanted.
Worth noting, a good password manager does more than just manage passwords. You can put secure notes about various things (like those stupid ‘security’ questions) or if you’ve linked an account or have multiple accounts which one this is, etc. Also by opening the site from the URL that you’ve stored in your password manager instead of clicking a link you’re much less likely to fall for phishing. And it’s easier - two clicks to open and login.
Re: Tips and things to avoid, it’s my personal opinion that I want to control that data myself and have it in a file that I can easily backup/transfer, so I don’t use a service or cloud solution or something built in to a browser. That means that you really have to make mirror copies (USB, phone, backup drive, etc.) in case you lose one (or more). But I prefer that. The networked solutions do get breached occasionally. The stuff should be encrypted, so that may be ok, but I’m skeptical.
VPN:
I’ve been using PIA Private Internet Access for a few years with no problems, though I don’t use it all that much. I mostly only use it when torrenting (which I don’t do much anymore since streaming has gotten so much better) or when I want to check something from another country (bypass regional media restrictions or check latency from there to a site I’m working on). I chose it because of their no-logging policy; getting a VPN for privacy is pointless if it logs everything you do (which some do).
If you’re not doing anything that’s mundane but that you need private (like torrenting) and the region traversal isn’t useful for you, I’m not entirely sure it’s worth the cost. I keep it around anyway, but I don’t really see it as a necessity. If you wanted to do ‘dark’ stuff, (buying drugs online, subverting an oppressive government, illegal porn), you’d want more than a VPN. But I don’t have recommendations for that.