There is a floor and a ceiling between which organizations must operate where information technology is involved. On the one hand, an organization must not operate below the floor and strain time and effectiveness because it lacks the technology to get things done correctly and quickly. On the other hand, an organization must not operate above the ceiling, relying on leading edge (and sometimes unproven) technology when a pen and paper will do. As to timing, you should know that most software is "buggy" when it is introduced and will improve as patches are added to correct things that initial programming did not. As to expense, if your organization is growing and your information technology needs are anticipated to also grow, consider leasing equipment instead of purchasing it. Also be cautious about offers to "trade-up" equipment after a few years. You might be surprised at how little the "electronic blue book" says your equipment is worth.