I've been using OVH for hosting for a couple years now. Their admin panel thingy is pretty confusing at first, but once you've set up bank transfer auto renewal you basically never have to look at it ever again, I pretty much do all my Server Management through SSH. Before that I've used both Digital Ocean and Microsoft Azure, which I'd recommend against. Digital Ocean is fine in terms of service and uptime and all that, but I find their price scaling unreasonable and they don't bother to keep their IP addresses clean, in case you were planning to be insane (host your own mail server). Microsoft Azure I only used because I had free credits through RuMoR and reemo scamming BizSpark lol. It was fine for the most part but at the time they didn't offer any rescue path in case you somehow were no longer able to access SSH (or RDP if you were using Windows Server). I actually did end up in a situation like this and I had to run various dodgy command line tools to download the VHD file for the server and extract what I needed via 7-zip...
For domain providers I've pretty much been using Namecheap from day one. They were indirectly recommended to me through many people and I think it's smart in the long run to separate where you have things signed up (like don't register it through a shared hoster or something like Cloudflare in case you ever wanted to move away from them). For the most part their name has rung true in my experience, generally being the cheapest option for the TLDs I want, except for .nl domains for which I use Strato. Strato's user experience is pretty poor and I had a similar confusing experience trying to figure out how to attach custom nameservers to my domains, but the domain I still have with them costs like 4 europesos a year so I can't really complain there. As for Namecheap, I have two complaints. I don't like their pushing of weird Blockchain stuff in the domain registration listing. They do point it out pretty clearly but I've gotten Sadness before trying to look up if a TLD is a thing only to be met with "Yes, but no" in the form of that weird Blockchain stuff. The other thing is that they don't let you authorise them to your bank or Paypal or whatever so you can't set and forget, you have to manually go in to renew every time. Some may see this as a feature but I just want to not think about it.
I started off self-hosting using an old Pentium 4 Dell, so the barrier to getting something running really is as low as that (provided your ISP isn't annoying about it). I use FreeDNS.afraid.org to get a free "domain" (basically a subdomain on a domain someone else is sharing) and I used them as my main DNS provider pretty much up until a point where they permabanned me an undisclosed reason, at which point I decided to just spin up my own DNS servers (it's cool but not exactly a recommended path). To lower the bar even further, I initially didn't even run Linux, I just had Windows Server with XAMPP, managing stuff through Remote Desktop Connection! I do definitely recommend eventually exploring Linux and how to do server management through the command line but go at your own pace, it needs to remain fun.
I do have somewhat of a media server but it's more multipurpose than that. It's a machine I bought off Matthew that runs Proxmox with multiple virtual machines, effectively creating my own VPS provider. My "media server" is just a Windows 10 VM with shared folders. I really need to migrate it over to Linux at some point but I very much cannot be bothered to move everything over... I use this machine for many other things as well, namely the game servers, development server for projects and I also host abyss.flash.moe from it. I originally used VMware ESXi because I doubted the capabilities of Proxmox and I was more comfortable in the VMware environment, but it really is the better option. It is a little bit more dodgy when it comes to Windows because the QEMU drivers leave to be desired, but it works well enough for running services from those operating systems. The LXC containers support it has is really great for running multiple Linux instances, as far as I'm aware the kernel is pretty much shared between each instance, so you don't have that overhead taking up resources, really neat in my opinion.
As for funny/interesting/nightmare-inducing experiences, I think I already named a couple in the previous paragraphs. Once I relaunch my blog over on flash.moe I plan on reposting the story of me running rm -rf * in the wrong folder and nuking my entire /www folder on the production server. As for fun/interesting ones, there's countless of those and I usually share them in chat when they happen, so I don't really have a concrete list to reference. It's a very multifaceted hobby so you run into a lot of stuff, I think.
I hope you pick up work on your website again, and maybe on that forum script as well! It's always cool to have other people work on stuff around you so you can share you experiences with them. The forum script kinda reminds me of the first one I wrote back in 2013, but yours is nowhere near as bad from what I can tell from the video lmao. I was too afraid of messing with databases at this point, so I just rewrote HTML files... Like, it works but it's not exactly workable in the long run. I still have a copy of the source code in case you want to take a peek: https://i.fii.moe/3IEUUH3LwGgAt2Y5fYibc5OtMW33XnmC. I created the repository at a later moment, so the README mentions a BiribiriBB 2, this eventually became the Sakura backend for Flashii. I sometimes semi-jokingly refer to Misuzu as BiribiriBB 3, might make this even more of a reality because I've been thinking of splitting the forum code out of the main repository and moving it to the forum.flashii.net subdomain but I am heavily digressing now so I will stop writing and post~
Oh man I completely forgot about Raspberry Pis. I literally have a 2, a 3 and a 4, I think I've used the 2 the most though they have their (had) their purposes. The 2 tends to be my go-to for low power stuff, I used to host a temperature page on my website which I'd use during the summer to see if my bedroom was liveable before I had an aircon. The heat got so bad that I'm pretty much my Yazawa Nico Nendoroid slightly melted as a result... I think I hosted Gogs/Gitea off of either it or the Raspberry Pi 3 for a bit, and it also hosted the Abyss at that point, I think. The Raspberry Pi 4 I literally only got because the CSE colleg I went to said you needed one (literally a 3 would've been fine...) but it has mostly been a ARM64 Windows testbox for me.
I don't think any of them have seen the light of day in 2 years.
Due to my studies I have more recent experience with AWS and Azure but for personal projects (https://tthew(dot)space)I pretty much exclusively use DO in containerized form ("Apps" as DO calls it). Not being a real programmer, I don't have much to host as most of my work is done at infrastructure level.
PSA: The opinions below are obviously exclusively from personal experience and in true Matthew fashion: short and unnuanced.
Combining these two as they are virtually the same service just with different branding. As mentioned above, the IaaS providers I have most experience with due to university projects, extensive offer of services, hellbent on locking you into their respective ecosystems. Cheap and decent performance with a plethora availability zones. I personally prefer AWS' web interface as to Azure feels like a convoluted mess where you can't find anything you want behind its 20 submenus. This could also be because of my limited understanding of cloud engineering when I had to use Azure. I would recommend these platforms for anything more complicated than web hosting.
The platform I started my server journey on. Never used this platform for more than hosting my personal website and Minecraft servers. Pricey VPSs but never really let me down. Very user friendly and a good starting point for but try to move towards a "better" one when you feel more comfortable with servers in general.
Decent pricing but high CPU latency. (also broke one of my mc servers once????)
Used this platform for a mere day before I got frustrated and dropped it. Worse than Azure category.
Namecheap.
Currently running a Raspberry Pi 3B+ as my personal project (internal tools) host. At the moment it's hosting a VPN to my home network, a web GUI Wake-On-Lan tool I made to RDP into my desktop in conjunction with aforementioned VPN, and DNS server. I don't really have a need for more horsepower. I don't plan on creating a media server as I don't really consume that much media outside of YouTube and I would be the only one using it (not worth the electricity). Perhaps in the future I'll change my mind when streaming services inevitably become evermore fragmented.

"OVH: Used this platform for a mere day before I got frustrated and dropped it. Worse than Azure category."
lmao I can definitely see that one. If my expectations went beyond "create server and use SSH forever" I'd definitely fall in the same category.
i don't do a lot (read: any) of web dev so i haven't spun up my own code, but i do host other shit that other people make because i like to use it! im also still learning a lot myself, but i'm still open to give my thoughts on things so far!
i've only used OVH mainly just from word of mouth, and i have the same experience as flash where i literally don't use it for anything except SSHing into it. the webUI is forgettable, the uptime is excellent. never had them go down on me in the year or so i've been using them.
used google domains before it got sold out, then went ahead and switched to namecheap, it's been fine beyond the aforementioned remembering that i need to pay for domains every year
not super often but i have and will self-host on an old computer/raspi, usually gameserver stuff since those in my mind are always much more expensive, and the VPS' i buy are generally worse (in hardware) than my raspis
probably soon! moving in with folks who are less tech savvy than me and it'll be useful to share files without going through google drive/discord (eugh) - i know they're not gonna do it.
i had to nuke everything once because i didn't know what i was doing and let down like 7 people.
causing problems on purposelol win i remember on the danooct1.com VPS i remember you have apt-get update/upgrade run weekly(?) as a cronjob and that made some of the Linux Inclined people Mad
will we ever get the Neeko webdev experience?