Long term goal would be to own half a dozen houses all in this neighborhood, mostly to build equity via mortgage paydowns, rather than excessive cashflow.Any objective thoughts would be welcomed.

On the 5th day at 5:00pm a $50 late fee is assessed and there’s a $50 late fee for all returned checks.

If all owed amounts are not paid in full by the 5th day of the month, a late fee of $XXX or XX% will be assessed.

I've read dozens of books, and they all seem to be directed toward the novice or wannabe investor What books are there for the almost-millionaire?  

Google it - as there are dozens on the internet that will do it for you

"Being cheap" is a bit of a harsh assessment I think.

Can you guys please help me in doing assessment to this property if I should buy it or not keeping in mind Canadian market.

Please tell us how - or otherwise we are then discriminating against the W2 tenant by having them comply with a proof of income.Seems that the federal gov't entities have identified a way to assess the income of those who are self-employed (see post by @Chris M.), and using those methods certainly cannot be classified as discriminatory. 

Its not necessary for average investors who own maybe a dozen pieces of real estate and assets under $1MIn California where lots of real estate is over $1M, people also use Trusts, and layered Trusts to make it difficult to find the real owner of a flipped house.

CA is not a poor rental market as that is an improper assessment in my opinion.