I hate it when he comes up with these things that are TOTALLY not economically feasible, then makes ME be the bad guy who has to point that out.
Is he really "making" you be the bad guy? Do you HAVE to point out the economic "infeasibility" immediately? If you did not point out the economic "infeasibility", would he be researching property in Nicaragua tonight and putting bids in on property by the end of the week? Or is he just voicing "wishes" out loud and talking more from emotion/frustration?
We're already in the hole from the paycut he took to join this startup.
Do I detect a bit of resentment? Be aware of that because it could spill out easily in a passive aggressive way if you are not careful. P/A behavior is not healthy for either of you.
Did he make that decision alone and without your support or did the two of you talk it over and did you give him your support for that decision?
In hindsight this startup may not have worked out but that does not mean it was not a worthwhile experience. From my experience I have learned as much from terrible management as from great management. While it has been frustrating, it is/was a worthwhile experience for your H and you!
I am so glad to hear your start-up is going well. What are you doing for yourself to keep your burn-out odds low?
Take care
But what is happiness except the simple harmony between a man and the life he leads? ~Albert Camus