Is it time to upgrade from free to affordable project management software?

One wise man once said that you get what you pay for.
Depending on who you ask, that man could have been either the 15th-century German philosopher Gabriel Biel or the novelist Kurt Vonnegut.
Greg Billings, our hero and president of Shady Acres Landscaping, Winsted, CT chose to follow the advice of an unknown, more frugal wise person.
Billings’ mantra regarding project management software was “If it isn’t free, then it aint for me.”
Billings maintained that the free project management software was sufficient, despite being advised by his field service managers.
He would exclaim, “If free software was enough to grow this business from a teenager mowing neighbor’s lawns to a 30-person operation with over 100 clients, I’ll damn if it wasn’t good enough for us now.”
This is the man who hosts the annual holiday party at the duckpin bowling alley. The owner is a client and allows him to use the party room free of charge. However, employees still had to pay $2 per shoe rental. Billings’ high-school nephew, The Sweater Daddies (ska-grunge fusion) provided musical entertainment in return for community service credits.
Billings would not pay for project management software if there was a cheaper alternative.
Unless, of course, someone made a compelling argument.

Affordable Project Management Software
Reba Greenway, Shady Acres most tech-savvy field manager, tried for years to convince her boss to move from, their free, open-source PM software, but to no avail. As their company grew, the software’s limitations became more obvious.
Crews showed up at worksite on the wrong day, because they didn’t communicate about deadlines. Because they didn’t use Gantt charts, workers would arrive to discover that the landscaping had been done by another crew. Because they were not managing their resources, teams arrived with only two weedwhackers to manage a five-acre lawn. This was all due to poor project management software.
Greenway stated, “I know how much money you like saving money,” Greenway said over lunch at a all-you-can-eat pizza buffet. “But this shoestring software has become a real headache. We are losing clients and botching jobs. It’s time for an upgrade!
He tried to deny it but he received enough angry calls to see that customer satisfaction was declining. He knew that his business would not succeed if it didn’t grow with its customer base. He wasn’t using the same Black & Decker push-mower he used 20 years ago. Maybe it was time for him to upgrade his software.
He said, “Alright, i’m listening,” as he wiped the marinara sauce Grade C from his mouth.
1. Alternative to expensive PM tools
Greenway waited for some rowdy children in party hats, to leave her booth, and then she eased into her pitch.
“Just because we choose to pay for project management software does not mean we have to spend a lot. She said that even for a small company like ours, a little money can make a big difference. We can try out several options with a free trial, and some–like Asana and Wrike—-remain free for small groups.”
Greenway’s point is supported by a Gartner report – Are Low-Cost or Open Source Project Management Tools Right For You? – which states that PM tools are often free to try or even free for a limited number of users. They may also be able to meet the PM needs for users with lower maturity.
2. Hidden costs of PM tools for free
Greenway asked, “How much money do we think we saved by using that open source software?”
Billings responded, “Well, I know zero per month is lower than any amount of dollars per monthly,” before taking a bite.