Additionally, since graduating, I have not held any sort of significant job in my desired career field and have been working a normal 9-5.  

My father left the carcass where it fell in the middle of an open field.

@Bill S. is right, I doubt there is much case law in the HOA field in Wyoming. 

And an unforeseen reason will only fly as far as a grumpy field auditor will allow it.Sorry, but claiming double top secret CIA status still may be your best bet - or 1031.  

I know this type of marketing is a field (and a job) unto itself - is it just not a great idea for someone in my position to be looking at this?

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We aren't particularly licensed in any particular field but we definitely are fast learners and pretty handy.  

But I do a little work in Chicago and the north side of Chicago around Wrigley field is RED HOT for 2 to 4 million dollar new builds  ( infill)

Is there a real benefit to getting this certificate if looking to grow in this field ?

However 1099 is very common practice in the medical field.