I would start by getting a look at what you're working with - paying for an inspector to visit isn't a bad idea, but depending on how much hoarding was done, it may be wise to remove some of the junk items first so they can give you a more accurate report. 

Recap: Tenant didn't pay rent for a few months, and we ended up in court, agreeing to a 12 month arrears payment (per courts).Today tenant received a DCA EPP Payment for 6 months into the future (May->Oct).

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Not only do you have to pay lawyers but you also have to pay an economist to write a report, pay the licensor and the list goes on.

If a put a down payment on a home and begin renting it out, is it okay if the property just pays for itself and I don't make any positive cashflow?

It seems like that they do not want to pay for the 45 dollars to go through it.

It was just a way to earn a few extra bucks when the circumstances proved right.The same for subject to deals; loan subordination; purchasing of “discounted” notes, or hard money lending.  

They owe me $1300, and I feel like they are trying to get by and just leave without paying me the rent that they owe.

From my experience, it seems that's why it's hard to find dependable cleaning & property management for STRs because it's a higher volume of turnover of guests, and property owners can only pay so much for management/cleaning.

Now you need to figure out how to find deals and pay for them.