Just make it simple for yourself. Do two SQL statements. One to insert and another to update.
INSERT INTO Table2 (OrderID, BikeValue)
SELECT Table1.OrderID, Table1.Value
FROM Table1 (NOLOCK)
WHERE Table1.Type = 'bike'
UPDATE Table2 SET Table2.SkateboardValue = Table1.Value
FROM Table2
INNER JOIN Table1 ON Table1.OrderID = Table2.OrderID
WHERE Table1.Type = 'skateboard'
与恶龙缠斗过久,自身亦成为恶龙;凝视深渊过久,深渊将回以凝视…