You have not added to much difficulty in terms of tax preparation, but in terms of tax record keeping you definitely have.I am not a tax professional, but having been a landlord who has tried(and failed) in my own tax situation, I would love to help point you in the right direction.Being your first year, it is all but a certainty that you have taken a loss.

What if a tenant fails to pay rent, leaves $2,000 in cleaning and repairs, and it takes another month to rent?

So it could take a decade to get to todays market rent. 2) it’s almost impossible if not impossible to non-renew a tenant, especially if you’re not an owner occupant. 3) As a seller, even if I could remove paying tenants I never would without a non-refundable payment from a potential buyer that covers all vacancies for 6 months if they fail to complete the purchase. 4) You MIGHT say as a buyer that’s worth it.

The #1 reason that Landlords fail, according to the American Apartment Owners' Association, is the landlord's failure to manage to the lease.  

Yes, I have a written agreement, bank records, plus phone records & email and text threads showing he routinely failed the SLAs outlined in the contract. 

They have failed to renew my entities with the Secretaries of State multiple times, have billed me wrong amounts, and GREATEST OF ALL, have cost my business ~$50K in cumulative TAX PENALTIES due to negligence in filing for a tax extension, failing to walk me through my tax filings and needed payments, and failing to file an abatement promptly.

Also, the contract that I signed failed to specify that the 1980’s house that I want isn’t a brand new house, so I’m glad that you pointed that out.

Later on people heard him saying that he wanted to kill himself due to all the failed deals.

Form 3115 allows you to restore the fairness in this situation and "catch up" with the remaining $30k of depreciation that you failed to take in the years past.

Quote from @Carson Hyland: Even if you buy the right property, failing to manage it well will kill your cash flow.