Guest-initiated upsell requests with host-set custom pricing

Problem statement

The current upsell system requires hosts to set fixed prices in advance for services like late check-out. This doesn't account for varying circumstances—such as occupancy levels, same-day turnovers, seasonal demand, or property-specific factors—that affect what hosts can reasonably charge. As a result, hosts either avoid using the upsell feature entirely or risk offering inappropriate pricing that doesn't reflect their actual availability or costs.

Current workaround

Hosts manage late check-out and similar requests entirely through manual chat:

• Guests ask for late check-out in the message thread
• Host replies with a custom price based on the specific circumstances
• Guest agrees or rejects via message
• Host manually confirms the arrangement in chat
• No automated payment collection or status tracking

Impact

• Creates significant friction and manual work for both hosts and guests
• No streamlined payment collection—hosts must use workarounds like Venmo or manual invoicing
• Increases risk of miscommunication or missed requests
• No automated confirmation or status updates for either party
• Prevents hosts from using Hospitable's upsell infrastructure for variable-price services

Proposed solution

Enable a guest-initiated request workflow for upsells where:

• Guest clicks a button to request the upsell (e.g., "Request Late Check-out")
• Host receives the request and inputs a custom price based on their specific circumstances
• Guest receives an automated notification with the price and can accept or decline
• System automatically sends confirmation messages to both parties and processes payment if accepted

Unlock

Hosts would be able to offer flexible, context-sensitive pricing for upsells like late check-out while maintaining a professional, automated workflow. This would eliminate manual chat negotiations, enable proper payment collection through Hospitable, and provide clear status tracking for both hosts and guests—making upsells practical for services that require variable pricing.