Get an idea of his expectations, that will help you tremendously in evaluating everything 

Research more than just warm areas - Central Oregon for example has a tremendous amount of tourism, is beautiful but we have cold winters that bring in a lot of business for the winter months of vacation rentals because of our skiing. 3.

If you have none of them, it will take a tremendous amount of hustle to succeed.It may be that your resources aren't sufficient in your current market, but that you may do better in a market with lower barriers to entry.

I was generally able to cover 30-60% of my mortgage expenses at any given time with the people I had living with me.Over then next 5 years or so, I poured a tremendous amount of sweat equity into the place.

Any experience on how to best navigate this would be tremendously helpful. 

After the approvals the value of the land increases tremendously especially if it marketed shovel ready for a builder..

I work from home and have tremendous flexibility with my hours.

It was a tremendous help in my investing business. 

In those scenarios I tend to suggest investing with developers that you find interesting and again, do your due diligence of course and eventually grow your portfolio through those means.So I wouldn't say you are "out of luck" you just have to decide if you want to commit tremendous time to it or if you prefer to keep life the way it is and invest passively. 

Thank you Brandon for being a tremendous source for real estate and lifestyle wisdom!