The value of buying a diamond in the rough is only captured if you do the labor yourself. When you have to hire out the work, the cost outweighs the beauty or usefulness of the diamond. So you have to evaluate yourself and know whether or not you will be able to follow through and if you have the patience and tolerance to live with your house in a less than perfect condition for a long time.
You may know how to do everything or at least able to learn how, but will you really want to do each job that needs to get done. You might enough woodwork, but despise electrical. So your floors will shine, but the lights won’t come on.
Also, factor in the mess that will surround you, day in and day out for eternity, while you try to muster enough energy at the end of a long day. Your day job takes a lot out of you, but to also try to tinker on some project for the house may not be possible some days. You must distance yourself from yourself and be honest with yourself.
Buy the diamond in the rough for a lower price than the value of other houses in the neighborhood, so that the overall value after renovations brings your house on par with the others. If yours is much higher, it may not do you well when it is time to sell. People negotiate toward the general value of properties in a neighborhood.