I just had friends/clients with a home to sell and the hopes to make a lateral buy ask me about timing and "to repair / or not…to repair?" For others in the same situation, here's my response. Glad to hear any comments.
There are a lot of moving parts, of course. When thinking of timing of sale and whether or not to repair, at least the following are relevant to consider in terms of cost/value:
-the quality of the market for sellers/buyers; you’ll be both (currently a seller’s advantage)
-any hurdles to selling (condition, location, etc) that a seller's advantage market will assist in leaping?
-disruption to the family unit (would you move 2x?)
-cost v value of repairs (I’m guessing I’ll suggest painting only; not roof and/or windows).
-cost of money for you as buyers (assuming you'll get a loan)