One word answer: Yes
Sure-you-want-to-bother answer: Think carefully in terms of materiality. If you have no external reporting obligation, think really seriously whether it makes any difference for your internal reporting. If you issue compiled, reviewed, or audited financial statements to outsiders, evaluate carefully whether the amounts involved are actually material.
What passes for a brief answer from a CPA: A few comments focused on small NPOs which won’t be complete or detailed. Please understand this is a high-level summary.
Here’s the overall answer: the costs of developing software that will be used internally by an organization should be capitalized, assuming the software isn’t going to be sold to others.
The accounting rules can be found in section 350-40 of the Accounting Standards Codification. The costs of purchasing the software or hiring a consultant to develop it should be included. Also included would be the time of your staff; however see answer #2 above. Include only costs incurred after developing the implementation plan and selecting the software or consultant. Capitalized costs include those to develop or install the software. Include cost of conversion of old data to the new system.
Training costs and on-going maintenance costs are expensed as you go. Don’t capitalize those items.
A detailed, technical answer: Call your CPA for more qualifications, exceptions, and hair-splitting details of previous answers.