I would assume that using the points for personal travel would be a conflict of interest (and illegal?)

I travelled down there last year and he was gracious enough to meet up and explain what he was doing down there.

Hey Brian, something I would look into is specifically renting out to traveling nurses and other medical professionals.

I've always been interested in tiny house living, or eventually buying an RV to travel, so living in about 1,100 square feet under this house hacking scenario would be a soft step towards towards that. 

They work long hours and make really good money (avg per hour is 25$) and they live in motels and hotels and travel trailer parks.

I feel similarly grateful for a lot of other people in other jobs, such as the ones who keep bathrooms clean in public places so that it is convenient for travelers.

They said thats fine as their friend who works for the city gave them the advice of medical excuse and they know it will work per his advice.

Commercial investors, for those of you looking for niches in which to invest, here's a blog I wrote on Medical Office Space.

He loves to travel, go on cruises etc, but I'm not sure if I get him cruise tickets it would be too much (going overboard).

I spent 20+ years with heavy travel in my professional life, then in my mid-40s we had a surprise family - which is being a wonderful experience :) A move into real-estate investing has allowed me to spend more time at home with my son - and to develop a software application aimed at building monitoring/management for landlords and their tenants.