This query only seems to fail under these very specific circumstances and when the last record has a null value in a search field.

orderby_issue.py

import arcpy
import os
import shutil
import tempfile

GDB_NAME = 'test.gdb'
FEATURE_CLASS_NAME = 'Widget'
FEATURE_CLASS_TYPE = 'POINT'
FEATURE_CLASS_FIELDS = (
    ('StaticID', 'LONG', None),
    ('QAComment', 'TEXT', 200),
)
FEATURE_CLASS_DATA = (
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (554030, None, (-2.0, 5.5)),
)
WHERE_1 = "QAComment LIKE 'Correct%' AND StaticID IN (103580, 554030)"
WHERE_2 = "StaticID IN (103580, 554030) AND QAComment LIKE 'Correct%'"
ORDER = 'ORDER BY StaticID ASC'

# Create a file geodatabase.
workspace = tempfile.mkdtemp()
gdb_path = os.path.join(workspace, GDB_NAME)
arcpy.CreateFileGDB_management(workspace, GDB_NAME)

# Create a feature class, and add fields.
arcpy.CreateFeatureclass_management(
    gdb_path, FEATURE_CLASS_NAME, FEATURE_CLASS_TYPE)
fc_path = os.path.join(gdb_path, FEATURE_CLASS_NAME)

for (field_name, field_type, field_precision) in FEATURE_CLASS_FIELDS:
    arcpy.AddField_management(
        fc_path, field_name, field_type, field_precision)

# Populate the feature class with two features.
field_names = [f[0] for f in FEATURE_CLASS_FIELDS] + ['SHAPE@XY']
cursor = arcpy.da.InsertCursor(fc_path, field_names)
for row in FEATURE_CLASS_DATA:
    cursor.insertRow(row)
del cursor

# Perform the test queries, and report the number of results.
search_fields = ['StaticID', 'QAComment']
for where in [WHERE_1, WHERE_2]:
    cursor = arcpy.da.SearchCursor(
        fc_path, search_fields, where, sql_clause=(None, ORDER))
    count = len(list(cursor))
    print 'Where Clause: %s' % (where,)
    print 'SQL Postfix: %s' % (ORDER,)
    print 'Count: %i' % (count,)
    print '\n'
    del cursor

# Clean up.
shutil.rmtree(workspace)

This issue only occurs when QAComment is null and part of the last expression evaluated.

Works:

FEATURE_CLASS_DATA = (
    (554030, None, (-2.0, 5.5)),
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
)

Works:

FEATURE_CLASS_DATA = (
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (554030, None, (-2.0, 5.5)),
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
)

Fails:

FEATURE_CLASS_DATA = (
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (554030, None, (-2.0, 5.5)),
)

Fails:

FEATURE_CLASS_DATA = (
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (103580, 'Correct Ramp Type', (2.5, 3.0)),
    (554030, None, (-2.0, 5.5)),
)