Hard to say without knowing the details of your finances (lean FIRE, fat FIRE, somewhere in between? Planned withdraw rate? Health insurance? Etc.).
When do you have to give a firm answer? Do you think the sale will be fairly secure (or likely dead) by that point? it would be hard for me to give up six figures for an additional month or two of work, and you can always get a cheap airbnb locally for that time. And you mention specific areas at specific times; would staying through mid-October cause you to miss something specific and that you can't do later?
I'd likely hedge my bets for as long as possible and then when the drop-dead date for a decision came, if the sale still looked likely, I'd bit the bullet and stay through October but if the sale fell through, that would be it for me. So I'd have a hard deadline.
One more thing... would a nice boss be willing to grant you some sort of remote work so you could perhaps commit to staying through mid-September if he promises to keep you on remotely (so you could start your travel) until the completion of the sale (or the end of 2019, perhaps; whichever is later)? It sounds like he really wants you to stay so you could negotiate to see if you can give a little (staying another month) if he gives (keeping you on remotely for 1-3 months).
- We are currently in the accumulation stages but plan to FIRE when I hit 55 in 23 years. We (me-32, DW-26) have $185k in retirement accounts. We will be receiving roughly $50k from the sale of the house once it is finalized and have enough money saved to have 6-12 months of expenses once we return even though I will be working for my father once we come back from the trip.
- There is no firm date on their end for me to provide a date. Multiple members of the company have spoken with me about my shares after giving my notice so that I am fully aware of the situation and they are open to me staying as long as necessary.
- We are searching on airBNB and the like but our area of Ohio doesn't really have a lot in the way of these rentals so we haven't found any options yet for an extended rental.
- Timing of events, yes, these are specific locations and events that we would not be able to do unless we extend our travels or delay them until this time next year which isn't feasible.
- For hedging - this is where I continue to have issues. I feel as though I/we would be stuck if we get all the way through October and are told that the deal is only two weeks away. Then rather/rinse/repeat and it continues is a possibility.
- Remoting - I posed this question to our majority shareholders (PE guys) and they were firmly against it stating that it is unfair to the other shareholders which I agree. Our trip is purely for pleasure and I don't want to give any notion that I would be working remotely.
- Caveat - one thing that I haven't addressed yet as I just found out while reviewing the employee handbook is that we have an extended leave policy that allows an employee to leave for unpaid leave for up to six weeks. I do not believe that this will work as I have given my notice and they understand that I have no intention to return but thought that it will be something to discuss. The CEO said that more information would be available by the end of this week to early next and he will provide me more clarity on timing so I thought then would be a good time to address this.