I have been running websites since 1995, and I can easily say the biggest headache I have had over the years is web hosting. For the first few years I used shared web hosting, but eventually my sites got big enough so I needed a dedicated server. Ever since then, it has been one problem after another. I started with 4 dedicated Linux servers and but they kept getting overloaded and crashing, so I kept buying new servers (they cost around $99/month each). I was always worried about overloading the servers, so I eventually bought around 50 of them.
Managing 50 servers was a nightmare. Not a day would go by where there was not a technical problem on one of my sites or servers. Server error, hackers, hard drive failures, bandwidth over-usage, faulty equipment, memory overloads, etc. As server technology improved, I eventually consolidated my sites to 5 servers, but then those same types of problems continued. Over the years I had tried several hosts who said they would manage the servers for me, like detecting when a server was down and then fixing it, but none of them ever did what they promised.
Tech support is always a big issue with any web host. Most of the hosts I used had horrible tech support. My sites would sometime be down for over 24 hours just because tech support was too incompetent to fix things. Other hosts have great tech support, but their hardware or network constantly has problems.
I currently have all my servers hosted at Colo4jax.com. They are a small host, but I like how they are able to customize my servers and they offer great tech support. The main reason I like them though is that they are cheap. I still have just as many problems with them as I had with my other hosts, but I feel much better about it because I am paying 25%-50% less than I used to pay. Here are 2 examples of hosting problems I had to deal with:
1. After a year or two hosting with colo4jax.com with no major problems, their entire network was down for 2 days because they moved to a new datacenter and had some problems with the move. All my sites were down, and other customers were posting in a forum that colo4jax might be out of business or that all the servers were lost. In the end, everything started working again, but it was a stressful 2 days.
2. Last week Colo4jax.com informed me that they immediately had to change the IP addresses on 2 of my 5 servers. Colo4jax was being forced to do this by their upstream provider, so it was not their fault, but it was still a big pain in the ass for me. I manually had to edit several hundred DNS entries to make this change. Then, to make matters worse, the next day my 3 remaining servers all stopped working. I realized right away that the problem was probably that these also needed new IP addresses, even though the old ones were supposed to still keep working fine, so I then had to spend another few hours manually editing several hundred more dns entries, plus my servers were down for around 8 hours.
Yes, after all of this I still recommend colo4jax.com because these types of problems happen with all hosts, so you might as well go with the lowest priced host. If you just have a small site, you can have it hosted on a shared server like at godaddy.com or pair.com, and you should have very few problems.
When I sold Bored.com in 2008, the buyer told me he was talking with a web host that would do his hosting for $8000/month and that $2000/month of that price was for managing his sites/servers. I told him no matter how good it sounded, hosting would still be a huge problem for him. After a year of that, he still had all the same types of problems I did, so he ended up canceling the management part of the hosting deal.
My advice to anyone looking for hosting is first to look on various web hosting review sites (I created one of my own at FindHosts.com) for reviews about whatever web host you are considering. Then, after you choose a host, hire a server monitoring and management company. They usually charge around $50/month to manage your server. I use Assistanz.com, but here are some others you might want to look at (I have never used any of them though): platinumservermanagement.com, acunettmanagement.com, and bobcares.com.