The five questions
1. What’s your total monthly software spend — all of it?
Add every subscription that runs the operation: the field platform, the extra seats, the add-ons, the form tool, the scheduling tool. Under ~$200 a month and it fits you well: keep renting. At $800–$2,400 a month (a common range at published and user-reported prices), three years of rent is $30,000–$86,000 — more than building your own.
2. Have you changed how you work to suit the software?
If your crew keeps a parallel system of texts, whiteboards and spreadsheets because “the app doesn’t do it that way,” you’re paying for software AND working around it. That workaround tax is usually bigger than the subscription.
3. How many tools does one job touch?
A quote in one tool, scheduling in another, invoicing in a third, the customer asking for updates by text: every gap between tools is retyping and dropped balls. Consolidation is the strongest case for custom — one place, one record of truth, your rules.
4. Does growth cost you software money?
Per-seat pricing means hiring has a software line item: $29–$35 per user per month at published Jobber/Housecall Pro rates, and ServiceTitan users report $245–$500 per tech. On a system you own, the new hire’s login is free.
5. Would it hurt if the vendor repriced, changed, or shut down the product?
Renters inherit every pricing decision (QuickBooks raised its plans in August 2026) and every product decision. Owners don’t.
The honest scorecard
Zero or one “yes” → stay off-the-shelf, sincerely. Two or three → get a quote and compare it to three years of your current bill before renewing anything (the three-year math, line by line →). Four or five → you’re already paying custom-software money; you’re just not getting the system for it.