This is a very tricky set of calculations because it is very personal; the truth is
The Higher the Risk, The Higher the Reward, but what each person is willing to risk is vastly different.
Myself, I do not have insurance on anything except my vehicles, and then only liability because that is law. Since I own my houses, I can determine what I insure. For some people that risk is too much, but I also have three homes, so if one was to be destroyed by fire, I could move into another house tomorrow. I would still lost the contents, but then again full coverage, on three houses, is a lot of money per year, and I have already saved enough money over the years to buy most of what I need to survive for another day. Again, some people could not possibly live like that, but I can, so I reap some financial benefit from it.
The other difficult part of these calculations is theoretical calculations and cold hard cash. For instance, I can tell you by
experience that converting
land from forest to tillable field costs $201 per acre, and that in less then one year, there is return on investment. However I must be able to take that new crop of
hay and
sell it in order for that to work, or convert that hay into
feed for my sheep that they convert into lamb that is old at the slaughterhouse, for it to be true. Just because grass is out in the field and has value, does not mean it is worth cold hard cash until it is harvested and sold. That is a big difference.
Then there is
cash flow. Again, there is a vast difference between theoretical and reality. A case in point is one of my houses. I am taking it out of rental as a residence and going in a different direction with it, even though that secondary function will yield less money per month then as if it was a house for someone to live in. Why? Because people assume that a house will be rented 100% of the time, and that is just not the case. When a person calculates the months that the house sits idle between tenants, other uses suddenly look more fiscally attractive. There are other aspects to look at as well, but the point is;
less is often more...in the long run.
It is often not the case with education. I worked at a shipyard where we I was paid over 50 cents a minute, and over a dollar a minute with overtime as a welder. I had no education outside of high school, and from day one, was able to start keeping all the money that I made. I invested in houses and land, but that is another story. Today times are changing. A town near me had their plumber retire and they could not get one in town, so they put out a bid for a plumber with a sign-on bonus of $7000. Now people might scoff at that, but they were not looking for computer tech's. That was a career that was in high demand when I was in school, but they are a dime a dozen now. If the trend towards free education continues, those careers will be saturated while skilled labor will be in higher demand due to baby-boomers retiring out. At 42 I retired, but have been asked to rejoin the railroad: no thanks...
(My career path was construction to railroad, to merchant marine, to ship building)