So how much can they lose that doesn’t cause: kids can’t go to college, have to sell their house, no more dinners out, etc   Determine their failure level or risk tolerance 5.  

1.ii - There's no concrete reason to self-employ in this path, but as it's the most risk-adverse it seems the most tolerable to act 'risky'.

Once this is done use the probabilities to build a portfolio around your tolerance for risk, need for cash flow, capital appreciation or capital preservation.

Once you've got a handle on that via a thorough analysis of the data you can make educated decisions in relationship to your personal goals and risk tolerance.  

Both jobs were made more tolerable with disposible rubber gloves and the mechanics gloves are the right weight, the right fit, and the right cost.The shop vac got used to vacuum hair out of the vents, a piece of broken glass out of the garbage disposal, and little shavings of new vinyl floor where the edges were trimmed to fit uneven walls.

Automotive tolerances electrical systems, computer systems are much harder than general construction.

i'd avoid annual seed mixes, and go for a DWARF PERENNIAL seed mix. it will theoretically require less frequent cuts.and im my semi arid coastal SoCal area,  only use mixes labeled 'drought tolerant'.

We aren't looking for this to last forever, as I know that painting tile isn't ideal, but just something to make it tolerable until we have the money to fully renovate.

Eddy investor, if he is at a point of making investments with his own money, clearly has an idea of what his risk tolerance is.

Is it worth it, I think that depends on your risk tolerance and what you are taking home from your day job.