Why not just go with shared hosting? It doesn't seem like you need something huge. You can get 5gb of space, with unlimited transfer for $5/month. You could always just upgrade the disk space if needed.
Some hosting companies can upgrade you from shared to VPS to dedicated with little or no downtime. I know who i'm with doesn't charge, and does it within minutes. It just takes a phone call or an email.
I would suggest getting a hosting company that won't charge you to upgrade.
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I rather have root access, and shared servers aren't the most reliable :/
That really depends on the hosting company. Some shared servers are super reliable without a huge price difference. But if you need root access, then yes, you need at least a VPS.
Do you know your way around a server through the command line or do you have to have a control panel? You can get some pretty good deals on some VPS's without control panels and meet your requirements.
I need to learn some command line stuff. I saw some VPSs from Spoilt.com and they were starting at about 10 bucks/month for what I needed. Would anyone be able to help me, linking me to a tutorial or something? I need to know how to get it all working.
Typically with VPS providers I have learned that you get what you pay for and there is so much control over resources, that although they appear to offer a VPS at a great price, somtimes they host will bottleneck other resources.