When looking at my tax return from my CPA, the losses and gains show up on Form 4797 (Part I for the losses and the gain in Part III).I noticed that the loss from Part I was shown on schedule 1 line 4. and helped zero my taxable income in Form 1040 line 15 (I had a negative total income on line 9 and 11).

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I wasn't really thrilled being forced to quickbooks online from desktop so I would like a different software for bookkeeping but need to retain my mortgage bank too. 

Private lending platforms and some online real estate networks also list these types of cash-only opportunities.

I am very weary of online places because it is very hard to vet out a company.

So a ways off from posting my mid-term rental online. 

Hey @Tarcizio Goncalves, QuickBooks Online allows for everything you need. 

Try to work or internship under a local property management company to get some training and learn the ins and outs of it.

Quote from @Xin-Ran Jiang: I just attended their orientation seminar today in NYC but didn’t sign up for 3-day train. 

Lots of material online.