If you're deciding how aggressive to be, anchor it to what homes actually closed for.
You're trying to decide how firm to be on price and terms without overpaying. My rule of thumb in Old Naples, FL right now build your offer around what recent closings indicate buyers actually secured, not what a seller hopes to get.
If you only remember one closed data point right now, make it this recent offers landed about 92.7% of asking last month, and a typical sale took 68 days last month for homes tracked in this market area. That matters because it sets expectations for both negotiation and patience. Some metrics were not reported for this period, but these two numbers alone tell me you should treat asking price as a starting point, and treat the timeline as something you manage proactively rather than react to. Write your offer plan with two lanes one lane for homes that are priced credibly and one lane for homes that are not, because recent closings at 92.7% of asking support a disciplined starting position. Set your personal walk-away number before you tour, then use the home-specific timeline risk to justify it when you negotiate in Old Naples, FL. If you need occupancy flexibility, ask for it up front and keep the rest of the terms clean so you do not lose leverage while a typical deal can take 68 days to close.
