I'm wondering if luxury properties are the way to go because a) better tax savings; and b) more likely to rent for $$$ during ski season, or at least that's what seems to be the case.

(Luxury, first time home buyers, investors, etc)There are several others that may be specific to yourself but only you can decide your final goal.

Thank you to all for taking the time.It's not luxury by any means, but for the properties I have seen in the neighborhood, I truly do believe it is in better shape than 90% in the specific neighborhood at least - 1960s neighborhood, covers whole sq mile. 3b1b 850sqft, "normal sized front yard" (for the area) 1,000sqft front yard and largest backyard in the neighborhood at 5000sqft. 

This would be modest build grade finishes, nothing luxurious, but not bargain basement, either.

@Jason Guenther Not sure of what is available in your market, but I downsized from a large Victorian mansion to a duplex 5 years ago.

I personally am almost always willing to sell a property I own if (1) I can created a ultra high ROI by use of seller financing/wrap loan with an existing loan that has a low rate or (2) sell for a low cap rate for a property without great upside potential and can reinvest for a much higher ROI.  

This portfolio consisted of around 80 single-family homes, some mobile home parks, a commercial building, some multifamily, and some luxury short-term rentals.I started getting a lot of people reaching out to me and asking me questions about real estate and if I would help them learn how to invest.

The luxury market in Miami and Palm Beach adds extra stability.

If he didn't have this luxury he would have hired a PM.    

Key for todays market is knowing your strategy with ultra detailed methodical planning, supported by solid data for viability, master of analysis, and action ready on the drop of a dime.