The right plan depends on four things: how many sites you run, how much traffic they get, how much space they need, and how demanding the software is.
WHAT USUALLY DECIDES IT
Number of websites. Entry plans typically host one. If you run several, or build sites for clients, you need a plan that allows multiple domains. Disk space and inodes. A brochure site uses very little. A media-heavy site, a shop with thousands of product images, or several mailboxes with years of attachments use a great deal. Traffic and resources. Shared plans include CPU, memory and entry-process allowances. A busy shop consumes far more per visitor than a static site. Email volume. Mailboxes draw from the same disk space as your website.
A REASONABLE STARTING POINT
Most new sites are comfortable on an entry or mid plan. You can upgrade at any time without moving servers or suffering downtime, so there is little value in over-buying at the start.
WHEN SHARED IS NOT ENOUGH
If you consistently hit resource limits after enabling caching and removing heavy plugins, or you need root access or custom server software, look at a VPS.
Open a ticket describing what you plan to run and we will give you an honest recommendation.