It really depends on how much you know, but more importantly how much you have created. With each creation comes experience and the problem-solving capabilities to tackle the problems you will have. I sometimes seek out information for how things are done on other game platforms. In the end, it's the same thought process, just different code. For instance, I look for topics on projects in Unity and Gmod when there's no information on ROBLOX.
Since ROBLOX made the UIConstraint system it would make the grid process easier.
If you're going to be able to search for items, then you're going to need to use string patterns and gmatch.
You'll need to create stats to track each item and their quantity, as well as save those later.
You'll need to equip and or drop items from the GUI to the world or player.
I would also take a look at how ROBLOX created their PlayerList GUI. The way they use tables is a good way to organize each item you index in your GUI.
In the end, it's just an ImageButton and a number that tracks what you have based on a stat. Whatever function you end up tying to that ImageButton is simply based on whether that stat is more than 0.
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WOW I had no idea ROBLOX added grid layouts, this is so handy, thanks! I know how to equp/unequip or drop items into the workspace, probably the only thing I am having trouble with is picking items up and actually placing them into the empty slots within the inventory.
I was really just thinking about something of this nature: http://i.imgur.com/P3VlWxd.jpg It seems quite simple, there are no weight or size restrictions on items, each item takes up a single slot, can be dropped, equipped and rearranged within the inventory.