When is turning a house into a duplex a good idea?

[Andra Tom]

I have a 1940 4+ bedroom house in Dallas, Oregon that I am not sure what to do with. I recently left my job and am trying to start my own short term rental services business but it’s slow going. So money is tight. My long term goal is to have my own properties either as STR or LTR. My options with the house are 1. Sell it - I have about $100000 in equity. But with no job I would have a hard time buying something else. 2. Rent it as a long term rental as is - I could probably rent it for around $1500, the mortgage, taxes & insurance are $1225 with 15% for vacancy, capx and repairs, I would break even. 3. It was a duplex at one time with the top floor being an apartment. I could turn it back into a duplex. That would involve putting all of the rehab costs on credit cards. I would have to put the kitchen back in upstairs leaving it as a 2 bedroom 1 1/2 bath apartment. The downstairs if left as is would have 1 bedroom 1 bath on the main floor and a full basement with a noconforming 1 bed 1 bath because the ceilings are not quite high enough. I can move the kitchen into the large living room to create 2 regular bedrooms on the main floor (another option). I could get $950-1050 for the upstairs and $1200-$1300 for the main floor. But I would have a lot to pay back on credit cards. I’m stuck in analysis paralysis. I apologize for the long post but any advice would be appreciated 😊🙏