Hey @Matt Oberski, VA's are a very affordable solution to getting your time back and focusing on the income-producing tasks in your business.

Over the last 15 or so years I have slowly and cautiously build a small portfolio of income producing real estate.

(There are services that will write and produce them if you lack the skills or time and advertising often will make it profitable.)Moving out older and smaller homes and replacing them with new and larger homes that are more attractive to higher income buyers and residents is always the primary strategy, unless you have a special market situation.

waste of time. further since your hubby is a self made millionare then I suspect like others said your social circle will be well off folks who own expensive homes.. you become a realtor and start listing their homes.. and selling them homes.. much better shelf life .. wholesaling is very intensive and hard to do.. you get on a top producer team and you will make money while you learn..

For ski areas, you may experience a hotter winter than expected which means not only will it not snow, but the resorts wont be able to produce fake snow either.

You are young, you have time, buy in the location that is going to produce the most "value" to you.  

I am looking to add high quality assets that produce maximum cash flow when paid off.

We also plan to open up 10 more income producing available lots within the next year.

Holding farm land or timber land would be better because it produces income.

Even if the price of real estate goes down you're still left with a producing asset (assuming you bought something that actually cash flows).