This excludes the cost of cleaning, which I've outsourced and passed the fees directly onto the guests at time of booking.  

I know that I’ll want to at the very least have someone in house if I can’t outsource the management.

lol the only advice I offered was to outsource the customer interaction / listing portion of your STR.

Bookkeeping is their wheelhouse.Salary/payroll/employment tax returns can easily be outsourced to third party platforms (e.g.

We all know we are suppose to work on the big "$100/hr" tasks and outsource the "$10/hr" tasks.

3) I'd go with Vacancy of 8.33% as this will mean you save up one month of rent every 12 months, 4) 3% repairs seems low, if it were me I'd at least bump it up to 5%, and 5) even though you plan to live there and self-manage there may come a day where you want/need to outsource management of your properties so it's usually a good idea to budget for management costs like @Doug Shapiro was saying.

He does outsource almost all labor (cleaning, mowing, shoveling, trades work). 

It makes me go crazy because I want to offer excellent service, but then having to outsource and worse, wait an extra day or more because the guy I called is booked.Has anyone else gone through similar feels?

@Patrick Britton if you use a contractor who outsources most of the tasks, your looking at an extra 10-15k overall

Sounds like you have your entire financial operations outsourced, in your words 95% of the day to day operations.