css :hover pseudo-class not working

If I'm guessing correctly what you're trying to do, then you don't need to change the positioning or any of that. The only change I can see you wanting to make is changing the background color. Here's the fiddle I made to clarify that response.

Here's the code for readability's sake:

HTML

<div class="wrapper">
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
    <br>
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
    <div class="squareswrapsolo"></div>
</div>​

CSS

.wrapper {
    height: 600px;
    width: 600px;
    overflow: hidden;
    position: relative;
}

.squareswrapsolo {
    height: 100px;
    width: 100px;
    display: inline-block;
    overflow: hidden;
    background: #ccc;
}
.squareswrapsolo:hover {
    background: #000;
}​

For me The problem was with my Chrome setting, I was testing my multi-platform web application with chrome in Mobile view for which the hover event is by-default disabled. You can disable the Mobile mode by clicking the mobile icon in the top-left of Elements tabs as shown in image.

Moreover, to check if your :hover event is setting the desired css property or not you can force-trigger the hover event from chrome (by checking hover in styles> :hov> hover red marked in image) and check if the :hover CSS property is working or not. For me it was working fine so I was sure that the event is not triggering.

In some cases (mostly with absolute positioning), you cannot apply a :hover pseudo-class to something with display: inline-block;. (If you have Chrome, use inspect element and add the :hover trait yourself--notice, it will work perfectly! The browser just doesn't register the :hover itself.)

So, I went ahead and replaced this with float: left;, added a margin (to simulate the inline-block look), and changed the br to a clear. The result is in this jsFiddle.