My father-in-law flies a lot and gets a lot of frequent flier miles. We might could drop him a hint, and he might would help us.

source: 
Montgomery
Entry: 
209
Example: 
My father-in-law flies a lot and gets a lot of frequent flier miles. We might could drop him a hint, and he might would help us.
Modal 1: 
might
Modal 2: 
could
Gender: 
Male
Race/Ethnicity: 
White
Age: 
24
Level of Education: 
Graduate school (Some)
Home Community, Town, or State: 
MS (Unknown)
Location Collected: 
SC (Unknown)
Relation to Addressee: 
Unknown
Medium: 
Spoken
Sentence Structure: 
1.1
Status: 
Naturalistic
Notes: 
Token also includes 'might would'