In this order.
hserout [whatever data, 13,10]

this will work all the time as long as you have sufficient delay between all your HSEROUT, and as long as your baudrate is accurate.

What you want is a ANSI terminal, those who accept ESC character, like the boring Hyperterminal, TeraTerm, RealTerm to name only but those. With an ANSI terminal, you can clear the screen, change font color, background color etc etc etc ( see http://www.pbpgroup.com/modules/wfse...hp?articleid=9 for reference)

Unfortunately, PICKIT USART tool is not an ANSI one, so you have to deal with the pain or work around. If you're a bit familiar with Microsoft C#, you could modify Pickit USART tool (as it is open source anyways) to accept ESC characters, or to clear the screen when you receive, let's say, ASCII 225 or whatever else. That should be easy.
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I'll redo my explanation about USART tool debugging...

Unless your current hardware don't use Serial communication, there's no need to use a switch, no need for HSEROUT either. What you do is to sit your PICKIT on the regular programming pins (MCLR, PGD, PGC) all the time, then you use DEBUG/SEROUT/SEROUT2 on PGD I/O. For this you must use TRUE mode.

Clear enough now?

I may try to post an example before going to sleep.