The truck was enabling me to do work on properties when that was not the highest and best use of my time.

No wrong or right answer but IMO I think the best dynasties draft good players (assets), develop the players (assets), and keep them. 

Those that are efficient and competitive will survive, the smaller players can't compete.      

They are in a different category than the legacy, bigger players like Buildium, AppFolio, etc in that they a design-driving team focused on usability around core features smaller landlords need most: automated rent collection, tenant screening, and electronic rental applications.

Each of these has been designed to cater to the different needs of property management professionals, helping to keep your business organized and your records meticulous.Buildium:Great for property managers handling a range of property types.Offers accounting, maintenance requests, leasing tools, and an online portal for tenants.AppFolio:Suitable for residential, commercial, student housing, and HOA property management.Provides features such as online rent payments, vacancy posting, maintenance requests, and accounting.Yardi Breeze:Ideal for smaller to mid-sized property managers and landlords.Features include accounting, operations, leasing, and rent collection.Propertyware:Designed for single-family and low-density residential properties.Offers customizable reports, maintenance, and inspection management.Cozy (now part of Apartments.com):Best for individual landlords rather than large property management companies.Features include listing properties, tenant screening, rent collection, and tracking expenses.Rent Manager:Good for managing a diverse portfolio of properties.Comes with a comprehensive set of tools including financial management, CRM, and reporting.RealPage:Suitable for larger firms with extensive property management needs.Provides solutions for revenue management, expense management, leasing, and more.MRI Software:Offers flexible solutions for real estate owners, operators, and occupiers.Includes tools for property-level management, accounting, and investment management.TenantCloud:Good for DIY landlords and property managers.Includes rent collection, tenant screening, and property maintenance features.Hemlane:A technology-enabled property management solution.Offers tools to advertise rental properties, screen applicants, and support local agents.I recommend exploring these options and taking advantage of any free trials they offer to find the software that best fits your needs.All the best with your property management endeavor.  

There are a lot of shady players in this industry, and with the market tightening up, I only anticipate the shadiness to become more prevalent.

YNAB does push people to prioritize money/goals and enable them to set money aside which enables them to achieve their goals much faster due to this clarity and focus.Case in point, I just had a friend who has been using Mint.com to track expenses for the past 1.5 years and just switched to YNAB in the last 2 months.

Overall Culture and Personality Fit - Are they a positive but realistic team player and on time to the meetings?

This enabled me to buy a single family residence 1 year later and then rent out the 4th unit which then paid for both of my mortgages.

I'm sure we'll see more shifting after Aug 1.Major players in the STR property management sphere have begun shutting their doors or shifting their business model away from STRs.