All risk no reward.
A solution to this dilemma for WITE and similar Russian Front games is to provide victory points or something for major cities and objectives and score players on how well they perform versus historical results. That way both players have strong incentive to perform better than history, throughout the entire war and not just focused on the endgame victory conditions. But, this scoring needs to happen periodically at say end of each year, with either just a result posted for players' information (for them to decide to end or continue the game) or some threshold for declaring a victory and ending the game.
Alternatively, house rules can be established to do the same thing. (Hint.) The old Avalon Hill boardgame The Russian campaign had a nice set of Sudden Death Victory Conditions:
24.3 SUDDEN DEATH VICTORY CONDITIONS:
Before the start of the game, each player must secretly write down an objective (city or oil well) for each year from 1942 through 1945—a total of four objectives for each player. At the start of the first clear weather turn of each year, each player reveals his objective for that year. A player wins IMMEDIATELY if at that point he controls both his own objective and his opponent's objective for that year.
24.4 If neither player controls both objectives, then there is no winner at that point and the game continues to the next year.
24.5 Each player must choose each year's objective from a list of possible objectives for that year. The Axis player must choose his 1942 objective from the Axis 1942 list of objectives, and the Russian player must choose his 1942 objective from the listed Russian 1942 objectives, etc.
24.6 In 1942, the Axis player may choose either Dnepropetrovsk, Bryansk or Leningrad. For 1943 he must choose either Leningrad, Kharkov or the oil well at PP13. For 1944 he must choose Sevastopol, Riga or Kiev. For 1945 he must choose Warsaw, Lwow—or he may choose as his objective eliminating the
24.7 For 1942, the Russian must choose either Sevastopol, Kalinin or Kharkov for his objective. For 1943, he must choose Voronezh, Moscow or Stalingrad.
For 1944, he must choose Leningrad, Rostov or Kursk. For 1945 he must choose Bucharest, Berlin—or he may choose to eliminate the Hitler counter as his objective.
24.8 If neither player has won by the second clear weather turn in 1945, use the Campaign Victory Conditions (24.1 above) to determine a winner—or a draw.
Alternatively, the Russian Front boardgame had a Victory Points Chart for checking victory level during every May and November Turn:
16.1.2 VICTORY LEVELS: After adjustment, if the victory level unit points to “0”, the game so far is a “tie”, otherwise check the “Victory Levels” columns on the VICTORY POINTS CHART, cross-gridding the current victory points shown on the CURRENT VICTORY LEVEL CHART with the current date. The letter found shows the level of victory, as follows:
D: Decisive victory for the side showing “+” victory points. The game is over and automatically ends at this point.
M: Marginal victory for the side showing “+” victory points. That side has an edge, but the outcome could still be reversed. The result can be accepted by mutual player agreement and the game can be ended at this point, or play can continue for another six-month period (unless this is Turn 42, and the game must end with a marginal victory result).
T: Tie. No one is winning, even though one side has some victory points. Like a marginal victory, the game may be ended here or continued (unless it is Turn 42).
16.1.3 HISTORIC VICTORY LEVELS: If desired, check the “HIS” column on the VICTORY POINTS CHART to see the victory points of the actual campaign (won decisively by the Soviet Union by May, 1944).
Point is, players do not have to reinvent the wheel here and can (should?) implement some modest house rules challenging both players to perform better than history all along the way.