One rule helped here (I simplify a lot): you should always count how much money will be left in your pocket after all expenses (including mortgage payments, taxes, fees, utilities, as well as the reserve fund for the current repairs of the property).

.-- Boulder County just simplified their rules to make it easier, in my opinion, to do STRs. -- Grand County, where Grand Lake is (also Winter Park), allows for vacation rentals pretty much unabated. -- Routt County, where Steamboat Springs is, has totally banned them.-- A little further south from you, the counties and cities around Denver are a little tougher on short-term rentals. -- Clear Creek County and Gilpin County both have caps on the number of Airbnbs and have met those caps. -- Jefferson County technically allows them but a county board has discretion over renewals, and I know of people being denied for what seem like arbitrary reasons.-- A little further from you, Park County is a great option.

Obviously I've rounded the edges of the process and simplified it a fair amount, but you get the gist.

I'm just trying to simplify the argument.Quick edit:  IMO, this country is broken in the sense that working hard and paying cash isn't rewarded anymore.  

Streamlined Rental Process:Renting to CityFHEPS tenants comes with a simplified rental process.

You should document the following items to satisfy the 250-hour requirement:Hours of servicesDescription of servicesDates such services were performedWho performed the serviceThe final safe harbor rules simplify requirements to substantiate time spent by employees and independent contractors.

This is a simplified calculation, and I would recommend you reach out to an experienced CPA who can account for all variables in coming up with tailored advice unique to your situation.Reach out if there are any further questions.

I understand the protection it provides, but there has to be a simplified way of doing this.

They simplified the process for us all while explaining to us in depth the important factors when buying a single family home.

Would appreciate if you could share any thoughts you have on this.https://www.biggerpockets.com/...I am selling my rental property with a 300,000 mortgage, and expecting to sell it in the range of 1,000,000, i.e. 30% LTV (simplified numbers with similar ratio).I am planning to reinvest in with 1031 exchange and have a bunch of questions on that.