One of the fastest ways to misprice a domain is to use end-user retail logic when buying from another investor, or investor-liquidation logic when a strong operating buyer arrives.
Wholesale is about margin and liquidity
An investor needs room for holding time, renewals, uncertainty and profit. Wholesale value therefore reflects a discounted exit where the next buyer also understands the resale risk.
Retail is about utility
An end user may care about trust, memorability, type-in behavior, naming simplicity, brand authority or lead-generation economics. The domain can be worth materially more to that user than to another reseller.
Your basis connects the two
Buying at a disciplined wholesale basis gives you optionality: wholesale liquidity if needed, patient retail upside if the right buyer appears, and development value if you decide to build.