How much of the S8 rent is covered by the program and how much is the tenant's responsibility is dependent on how much money the tenant makes.The housing department has a formula they use to determine the voucher mix.

It shouldn't be too much money to get it cleaned out.

I feel like I should transfer some personal funds to make sure this property is well covered before I purchase my next rental property. 

And you need to weigh those pros and cons to make sure Section 8 investing is the right decision for you personally.

I personally don't work with clients in Canada but would highly recommend someone who works with clients in Canada and US.

Where I do agree with James, but this is Section 8 or not, there are somethings that cost more initially but will save you a lot of money over long run.  

You are going to have to get personal with your team so they can structure something that works for you personally. 

Should I take out equity in the home towards a crash pad and/or doing some minor upgrades on the home OR should I save up to get into air BNB arbitrage to increase my money flow and put that towards fixing the home and eventually obtaining a crash pad.

What makes a “good” deal can differ enormously from person to person.  

Difference this time for me is hard money and wholesalers, it has been interesting.