Tax Year Prior to 2020: Can a husband issue a Misc-1099 to his wife for money paid to her if they are filing separate?

[KarenL2]

Not usually.  Spouses do not issue 1099 forms to each other whether filing Jointly or Separately unless there is a specific business reason for it which is very rare.  If you each have separate businesses (legal entities), then your business entity could issue one to hers.  Otherwise, there is no reason to do it. 

Also, filing a 1099-MISC late results in penalties.  

"The penalty against the company varies from $30 to $100 per form ($500,000 maximum per year), depending on how long past the deadline the company issues the form.   If a company intentionally disregards the requirement to provide a correct payee statement, it is subject to a minimum penalty of $250 per statement, with no maximum. "

Is it better for a married couple to file jointly or separately?

https://ttlc.intuit.com/replies/3288477

Married Filing Separately in a Community Property State

https://ttlc.intuit.com/replies/3301943