First you needs to determine your investment philosophy.

I'm not sure if I agree with that philosophy.

I think he's applying the same philosophy to real estate that he does to stocks, which is that he's content to miss out on buying at the bottom IF he's convinced that prices are header higher.

If anyone else has a different solution or philosophy I'd like to hear it.

My prior philosophy had been since they are really good renters I would not want to jeopardize losing them  by proposing a rent increase but in the end that's not worth losing up to 4-5k every year.  

Our philosophy is that your profits are made on the buy.  

They are doing a lot of things right.Additionally, they just launched a new product/service where you can invest with a group of friends called Lofty Select: https://loftyai.notion.site/In...I'm very interested in finding other RE investors who align with my investing philosophies and goals to do a deal with.Read all of their help pages and blog posts and you'll know a lot about the platform.

My personal philosophy has always been ellimination of debt is the best investment.

My concern is that given the history and philosophy of the resort that the brokerage would not pass along any such incentive to the qualifying agent.I am hoping to tap into the vast knowledge, experience and creativity of this community for some ideas. 

I follow rich dad poor dads philosophy of using other people's money.