So the tenants keep paying my mortgage (went up by about $40), and I reap the rewards on the cash-flow. 

That's okay, they will be rewarded with riches for being good minions after they die.

style things into it, complete with easy rewards early on that get spread farther out as you progress so it remains rewarding.

I take some risks and I figure I get rewarded and not penalized! 

Seeing as I recently opened a business credit card and would prefer to utilize it for cash back rewards I'd like to use that to pay the contractor directly.I've brought it up to my property manager and he stated it's doable but recommended doing the payment through their portal so they can provide these repairs in a 12 month cash flow statement and have it as part of my 1099 at the end of the year to simplify taxes.

Their are, of course, rewards.  

The past 3 years of off market acquisition has been fun, rewarding and truly beneficial to all parties involved.

So as long as you understand the risks/rewards of condo investing, I do not think there is anything to be scared of.I would like to point out though that the market place can have an impact on the risks/rewards.

The credit partner has a lot of risk and you need to show them you have everything under control and that they are going to get rewarded for doing these transactions.

That being said, this is on track to be a very rewarding investment and would recommend self storage.