I have educated myself well and good at crunching numbers, but I lack the procedural experience that comes with deal making when it comes to multifamily.   

They make educated guesses about each and make their "bet". 

As I continue to analyze properties, it seems that the expenses are eating up a large portion of the cashflow, especially when utilities aren't separated. 

Usually minor things aren't going to get you much but major repair items will, like the roof needs replaced or it has cracked rafters or floor joists. 

If you go the in-class route for the continuing education as well, then since the school itself administers the test, the instructor literally gave us exactly what we needed to know since he was the one who made the test.

Lots of great Canadian real estate podcasts to continue your free education:-Truth about Real Estate Investing...for Canadians-Breakthrough Real Estate Investing-Where should I invest?

After being with this company for four months I’m feeling like they aren’t doing a good job.

Account Closed if you are using ‘actuals’, you aren’t being conservative.

They aren't a lender.

It is possible that a lender MAY not lend a VA loan over that threshold....lenders aren't insured as much by the VA once they reach that loan size but you'll see that you will be required to start bring a very small down payment over the $453k threshold.