Brian:
I don't have much time to give a proper solution; so as time is ticking I will put what I have so far.
SetSystemOptions["DataOptions" -> "ReturnQuantities" -> False];
ISOWeek[x_] :=
Module[{d2},
d2 = DateList[{ToExpression[
DateString[
DatePlus[
x, {(-(Flatten[
Position[{"Sunday", "Monday", "Tuesday", "Wednesday",
"Thursday", "Friday", "Saturday"},
DateString[DatePlus[x, {-1, "Day"}], {"DayName"}],
1]])[[1]] + 4), "Day"}], "Year"]], 1, 3, 0, 0, 0}];
IntegerPart[(DateDifference[d2, x] +
Flatten[Position[{"Sunday", "Monday", "Tuesday", "Wednesday",
"Thursday", "Friday", "Saturday"},
DateString[d2, {"DayName"}], 1]][[1]] + 5)/7]];
ISODay = Function[{date},
Flatten[Position[{"Sun", "Mon", "Tue", "Wed", "Thu", "Fri", "Sat"},
DateString[date, {"DayNameShort"}], 1]][[1]]];
Grid[{
{
Item[Style[
DateString[DateList[], {"Year", "", "Month", "", "Day"}],
FontFamily -> "Arial Black", FontWeight -> "Black",
FontSize -> 32], Alignment -> Center],
Item[Style[
StringJoin[
ToString[
IntegerPart[DateDifference[{First[DateList[]]}, DateList[]]]],
" / ", ToString[IntegerPart[
DateDifference[ DateList[], {Plus[First[DateList[]], 1]}]]]],
FontSize -> 28, FontFamily -> "Arial", FontWeight -> Bold],
Alignment -> Center],
Item[Style[
Row[{Style[StringJoin["WK", ToString[ISOWeek[DateList[]]]], Red],
Style[StringJoin["-",
ToString[
NumberForm[ISODay[DateList[]],
NumberPadding -> {"0", ""}]]], Black]}], FontSize -> 30,
FontFamily -> "Arial Black", FontWeight -> Bold],
Alignment -> Center]
},
{
Item[Style[
DateString[
DateList[], {"DayName", ", ", "MonthName", " ", "Day", "th, ",
"Year"}], FontSize -> 40, FontFamily -> "Calibri",
FontWeight -> Bold, FontColor -> White, Background -> Black],
Alignment -> Center, Background -> Black], SpanFromLeft,
SpanFromLeft
}, {
Row[
{
Item[
Style["Spring 30/63 (2nd)", FontSize -> 24,
FontFamily -> "Arial", FontWeight -> Bold],
Alignment -> Center], Spacer[50],
Item[Style[
StringJoin[DateString[DateList[], "Quarter"], "nd",
" Quarter ", "18/73 (3rd)"], FontSize -> 24,
FontFamily -> "Arial", FontWeight -> Bold], Alignment -> Center]
}, Alignment -> Center , Frame -> False
], SpanFromLeft, SpanFromLeft}
},
Frame -> True, FrameStyle -> Thickness[5], Spacings -> {2, 5}]
Which would give

The Seasons, Quarters, and dividers need more work. I had a version with Overlay[Grid[]...]. But that was unstable interns of screen resizing. There used to be a package that calculated Seasons
see Scientific Astronomer http://library.wolfram.com/infocenter/Conferences/372/
I attempted to get as close to your original fonts. It would be easier to explicitly state them. My font matching skills are rusty. I'll come back to this later.