How to trigger a follow up message for a LOST lead

Hey Team, I am back - You always super helpful, TY!

Scenario one:

We have a sales pipeline for HOTEL, we give out quotes, and then there are some bots automating follow up messages, ont he 3rd strike (msg) the lead/contact is close but when doing with automation always picks "undefined reason" wondering how can I manipulate the reason with some automations, for example if the contact says "out my budge" I would love for kommo to read budget, and if this lead gets closed, the bot closes "out of budget"

Scenario two:

Similarly, sometimes our contacts tell us right away, "cant affors it" and we then proceed say to close it an MANUALLY specified "out of budget" how could I trigger a message at a later time (based on custom field check in date" a message sending an offer "we know the last quote was out of budget, but we're willing to issue you a discount " IDEALLY the message goes out say 48 hours before their desired check in date.

Thanks!