If you don't mind me picking your brain for some generics, what's the general volume and scale of your operation?

This is anecdotal information based upon the interviews I’ve had with operators across the country.

As others have noted, it's not perfect (no software solution will be), but It does get the job done.

The contractor we hired renovated several other units in the same building and did a beautiful job.

one thing I didn't see in this thread is... do you WANT to own and operate an STR?! 

Once the home is a rental, you can deduct operating expenses like property taxes, mortgage interest, insurance, and depreciation (over 27.5 years for long-term rentals).

Now days you don't buy a deal you make the deal either with how you operate the property, how you finance the property, or how you purchase the property.

We're currently both working a W-2 job with a combined household income of roughly $150k, and searching how to start to our journey to financial freedom. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

It's not a magic bullet to solve all operational needs, but the process works very well when a remote team member at a lower labor rate fits into the needs of a scaling business.