Random map generation script not working!?

I recommend using lists/tables when dealing with multiple objects:

RoundStart = game.Workspace.RoundStart
--Initialize Rooms list
numRooms = 5
Rooms = {}
for i = 1, numRooms do
    Rooms[i] = game.ServerStorage["Room" .. i]
end

function NewMap()
    if RoundStart.Value then
        local randomRoom = math.random(1, 5)
        local map = Rooms[randomRoom]:Clone()
        map.Parent = workspace
    end
end

RoundStart.Value.Changed:connect(NewMap)

As you can see, using a list makes the NewMap function considerably smaller.

You might want to add RoundStart.Value = false somewhere in the NewMap function (within the 'if RoundStart.Value then` block).

1. Make the variables local
2. Is RoundStart being changed?

Local Variables

You need to do this because of this example.

local num = 0 --Variable

--What you are doing is this

test = 0 --This would mean that the variable test will be changed to 0. But in order to do this
--"test" will need to be an already existing variable.

--To let the script know you are making a new variable, put local behind it.

num = 1 --This will work since num was created on line 1.

Is the the RoundStart value being changed? Instead of using a value, call the function in the script.

function startround()
    print("Starting round!")
end

startround() --Calling the function right here in the script!

Here is the perfected script, that may need some fixing. You can fix the rest.

function NewMap()
       local  RandomRoom = game:GetService("ServerStorage"):FindFirstChild("Room"..math.random(1,5))
            if RandomRoom then
                    RandomRoom:clone().Parent = workspace
        end
        end
end

Hope this helps!