[tyger11]

If you can quantify the amount of time & expense between the two, you get your answer:

1) no rewrite but painful updates over x period of time (total) 2) painful rewrite but easy updates over x period of time (total)

If the delta is small between the two, then think about how long you intend x period of time to be - when does it make financial sense?

Also, be aware that painful update experience winds up costing you in developer turnover. This can be a HUGE cost.

Short term thinking of "it's too painful to do a rewrite" has killed more companies than I care to remember.

But you need to figure out how to glean realistic and correct numbers for these things to justify EITHER decision. Neither option is always right - and if someone is saying it is, that person needs to be jettisoned ASAP- they're poisoning your well of information.