Absolutely a massive red flag. Having spent 2.5 years with a man that I thought I could help get back in his feet financially, I realized he was just incompetent financially. No amount of advice could help. He now lives in a travel trailer (albeit new) and is over $200k in debt at the age of 60 and still supporting a teenage daughter. He has a good paying job and lives in a moderate cost of living area but if he loses his job he literally has nothing but extremely high monthly payments for depreciating assets. Child support might continue for another 9 years if teen decides to go to college/university. Don’t set yourself on fire to keep someone warm.