Sell or rent out again? I keep going back and forth...

[René Madsen]

I own a rental (single family home) purchased 10 years ago for $189,000 in south Florida. In an ok, but not good neighborhood. 

Current value is about $275-300,000 depending on how much work I’m putting in. I’m remodeling at the moment after the tenants moved out a month ago. 

I owe $150,000 at 5%. Mortgage, insurance, taxes and lawn services are $1370. Maintenance is extra. Roof will probably need replacing in 5-7 years. AC around the same time. 

I’m considering two options but are also open for other suggestions.

1. Cash out refinance (or Line of credit or?) and then rent it out again at $2100.

2. Sell it.

Either way I’d use the cash for a down payment on a “new” home for the family as we have outgrown our current house and then rent this one out as well.

The big capital expenditures (roof) are what scares me but then again paying fees for selling also adds up quickly.

I’m going back and forth, please help.