It would depend on what kind of shape the property is in of course, but personally I’d give it a shot listing it as soon as the tenant is out with an X dollar credit (probably less than I intend to spend on the remodel) towards the updates with a full price offer….maybe consider paint and carpet if it’s really bad. That way you get it on the market when more people are out looking (summer) from a demand standpoint. Spring is best, but Summer is good too though. A lot of people will look in the spring and summer (especially if they have kids in school) and if they do not find what they want they will give it another shot next year at the same time. Not always, but a lot of the time. One consideration is that some people have vision and their own particular style so they would appreciate the credit, but many other people do not have vision and you need to do it for them to see the potential.
You could gauge the activity with your Realtor and if it’s not in escrow in the first couple weeks to a month possibly reconsider and remodel the property at that time to get it sold.
I’ve always thought that Spring and Summer it’s best to be a seller and Fall-Winter it’s better to be a buyer from a macro perspective, but you would also want to have a closer look at your local inventory too at that time. You could list in the fall and be the only home available similar to yours in the area at your price point and that tends to be good too. Just find a Realtor that is willing to ride it out with you and has a bit of flexibility to work with you on your options a bit and what is best for you.
FYI- I am licensed, but I go to piggington for knowledge, feedback and to learn from others not to generate business. I work at a tech company these days. I just keep my license to help my wife out from time to time and because I enjoy the investment side of things. I’m sure you know 1000 realtors anyways as most people do.
I hope it plays out well for you and I’m thinking it will! Good luck.