Once a home inspection company gets their reporting system dialed in and is doing well, it can become increasingly difficult for them to make changes that reflect changes in the industry.
Part of this is due to hesitation on the part of a company owner to fool with something that has been working for a while, plus dealing with evaluating and choosing new software and the training involved, especially with multi-inspector firms.
It's also due to an increasing number of inspection software companies that have sold out to large companies whose primary interest is not in home inspection, but in data mining. There is a definite software industry trend toward moving from app-based (lives on your hard drive) to cloud-base (lives on their servers) software.
There are some great advantages to cloud-based software, but having inspection reports stored on their servers can give software companies access to data that other companies (think insurance and credit card to start with) are willing to pay for.
Tip-toeing between mud puddles refers to inspection companies trying to maintain their report quality while keeping them current with state of the inspection industry, which may mean switching to new software occasionally, while avoiding putting their client's data (and inspection company reputation) at risk.