Do you want a company that will keep the long-range investment objectives in mind or one that focuses on today and today's profit alone?     

Do you have the financial strength to hold/carry these lots if they don't sell quickly? 

Staying local and house hacking—especially now, before kids—gives you so much flexibility to set yourselves up for long-term success.Your financial foundation is super strong, and house hacking a quad sounds like an amazing first step for you two.

Trade some comfort for financial stability.Part of attaining financial success is being simultaneously optimistic and paranoid. 

Today Bitcoin is about $93,000, can you buy it today for a 35% discount or $60,450?

I have been out of the country and just seeing this today.

The existing number of vacation rentals are so far over those caps that anyone who gets on the wait list today will likely wait 5-10 years before they're up for a permit.I do think this is the natural progression of what is still a relatively new industry.

However, sometimes investing is more than just the financial return.  

Looking forward to building a better financial future.

Leveraging a property in todays environment of high interest rates will not get you cash flowing.