It gives you the power of a professional real estate bookkeeper but it's simple enough for someone who is not a fan of bookkeeping to stay on top of things because the User Experience is well thought out.

That's honestly an extremely simple process.

Don't be fooled by the returns you see on paper in the midwest.

Not a lot to add here, just the simple advice to make it as easy as possible to pay rent. 

Thanks for the colleague request.The concept of TDR is fairly simple and straightforward.

@Eric Coats, to answer your specific questions, estimating expenses are pretty simple. 

Tools like QuickBooks or even a simple spreadsheet can help you mentain compliance and prepare for audits.Reinvest WiselyScaling a short-term rental business often requires reinvestment in marketing, property upgrades, or even hiring help.

I also agree that RE appreciation is unlikely to match the last dozen years, but you never know.Where I am unsure we agree is that paying $450k to improve the cash flow ~$3k (your numbers but I expect my delta wold be similar meaning both my cash flow estimates would be worse than yours but both would be worse by the same amount not affecting the difference) makes sense especially if the cost of having the extra $450k is only 6% rate which is historically simple to beat via numerous investment options and hopefully no one is investing in RE for an expected of 6%.  

Yes, you bought what seems like a good deal on paper, but in reality, you own an old apartment building in a neighborhood with poor security, possibly surrounded by long-vacant shops, streets piled with garbage, and a poorly managed community.

In future if you are refinancing I would sometimes look to pay a higher purchse price but have seller concessions to bring the price down on paper but not for comp purposes.