Can I pay the contractor I found myself and just let them know the work is being done or is it best to run everything through the manager?

The slippery slope of late rent payments start with checks because there is less footprint on their actions to actually pay you and they can falsify dates. 

You simply have to be honest in all your dealings with people and make the proper licensing disclosures so there is no chance of confusing the “I am representing you as an agent verses I am representing myself as a principal in this transaction”

Back then there really weren't many options but I still feel that you can easily use excel and do not need to pay for these programs and pay a monthly fee.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

I'm not a cashflow is everything guy but I don't like taking money out of my pocket to pay bills. 

Sometimes it is best to pay the tenant to get her out of sight.

In addition, I pay a 1,000 finders fee to anyone who tells me about an unlisted house that I buy.

My reply didn’t quote properly.

I'm looking to pay cash since my job is not stable and move from one job to the next (i'm an artist).