We've developed short term property management software based on automations taken from guest messages.

@Austin Jones - As part of the BiggerPockets Pro Membership, you have access to Stessa's accounting and portfolio tracking software included with your membership.

Software is a self Manager's friend.

Simply get a password software like Lastpass or OnePassword account.

Does anyone know of a software to calculate medium term rentals?

I would add, make sure you have good landlord resources as you enter into the landlord domain-lease agreement fitting your situation-resources for your tenant application process -needed landlord forms and notices-education resources-management tools (e.g. software to keep all records, pictures, payment history, etc.)Best wishes.

The vast majority of tax preparers merely fill out forms you or their software tells them to fill out.

> When self-managing, are there any software or tools that are "must-haves" to make it less stressful for you? 

I would also encourage you to source leads through a software like TurboTenant which will streamline the process, in conjunction with the handouts found in Brandon's book, and likely provide a better applicant pool as your listing is automatically published to multiple rental listing sites.

Our son has a good software career that he enjoys but I hope this business will provide him the option of retiring early should he want to.