Age of Principals
Cross-purchase plans generally favor older owners; entity-purchase/stock redemption plans tend to favor younger owners.
Ownership interest
Cross-purchase plans tend to favor majority owners; entity-purchase/stock redemption plans generally favor minority owners.
Comparative tax brackets
For corporations, a cross-purchase plan may be more appropriate if the principals' individual tax brackets are lower than the corporate tax bracket. A stock redemption plan may be appropriate if the corporate tax bracket is lower than the owner/shareholders' individual tax brackets. If the business may be taking in new principals in the future, adjusting the insurance policies in a cross-purchase plan can be more complicated than under an entity-purchase/stock redemption plan.
Convertibility
Cross-purchase plans are readily converted to entity-purchase/stock redemption plans. Because of transfer-for-value problems, it is less attractive to convert entity-purchase/stock redemption plans to cross-purchase plans. Cross-purchase plans avoid IRS "attribution" rules that can create problems in family-owned corporations.