Hi Debby,
I asked around Construx for some ideas for you. Matt Peloquin replied with
Not what they're hoping for but I'd replace:
'when your maintenance costs too much'
With
'when your maintenance costs more than building a new system to produce equivalent value'
This is such an economics based question that it has to be answered by an analysis of cost of development vs. value in old vs. new system. Any rule of thumb heuristic not based in such an analysis seems glib to me.
Steve Tockey replied with
That's kinda where I was going with the "there's more to this", things that need to be considered in a true business case analysis would include:
How much is being spent now on maintaining the existing system (and future projections of same)
Cost of lost business flexibility because new functionality can't be added (...quickly enough)
Cost to redevelop the existing system
Expected reduction in maintenance cost following redevelopment
Business value of increased flexibility because new system is more maintainable
He also suggested that you look to his book Return on Software for was to calculate those decisions.