I’ve talked with several hedge fund managers lately about these risks, and everyone I talk to agrees that there needs to be a substantial return to make it worth it (assuming it’s purely for investment and not leisure).

I also actually really enjoy learning and getting to know people now so some of my 'leisure' time is spent on learning and networking...

It is in indeed, there are other leisurely activities like ice fishing and snowmobiling but it definitely slows down. 

After, it might be considered enjoying the time you've earned for yourself by putting people and systems in place to take care of your investments while you enjoy your leisure time.Your mention of returns, therefore, fails to take into account the value of your owntime IF you devote it to income-producing activities rather than leisure activities.

Word of advice, instead of talking about yourself and your leisure time travels. 

Then all bets are off.If you build or buy an STR now you are simply speculating going into a down turn (fact) at peak prices (fact) into a market space that is being devastated (fact) - travel and leisure business' are nonoperational in most of the country and the world and if not in your area now it will be tomorrow or the day after or next week.

Even if it's a non-profit the person has to put limits with their time on helping people learn the business so they can grow their own.This is why I like BP.People can log on at their leisure and learn something new everyday.No driving,no meal costs,no excessive drain on time for the day,no hard sell,etc.I or anyone else can post great information on here and tons can read it with new people everyday.

Didn't even think about going there because we've been having such success with AB&B and VRBO when we are offering our beach home as a vacation rental.It started out as a vacation property for our 5 children and 14 grandchildren and my wife and I to all share at our leisure.

I made sacrifices, how much fun and leisure time do you think one has doing College FT, working a FT job and a PT job?

My why's are:To be able to tithe more at churchTo be able to help my nephews pay for post-graduate educationTo have something to invest my time inTo not have to work in my 60s and upTo be able to help my brothers and nephews health concerns as they ageTo be an example of how one can start again financially at 40-50 and succeedTo have leisure time to travel, read, do needleworkTo share as much time with my brothers and my nephews as that and I wantTo donate to the care for the organ fund at churchTo assist women entrepreneurs in the US and abroadTo be able to donate at least one million dollars to the department of surgery at HUHTo donate at least one million dollars to Hoeard UniversityTo donate at least one million dollars to Howard University College of Medicine That's it for now!