(Looking for a wooden fence to be installed at a property). 

I certainly didn’t always have months and months of reserves, and the idea of 50% vacancy or tenants not paying would have been quite nerve racking.

The idea that "we won't be able to pay off the debt anyway, just keep racking it up" is a slippery slope. 

When you rack up a lot of debt the bank will tell you to pay it off so you can buy the next deal and then you’ll pay it off with the extra income that you’ll be making from the investment.

Unfortunately many schools don't have these programs available any more, but I would say this was a huge factor in my ability to quickly learn how to fix houses and even analyze rehabs, manage contractors, spot when things weren't being done correctly by said contractors, etc.While most of my friends were in college partying, racking up $50k+ in debt only to have a useless degree that they never ended up using, I was making $50k+ a year working blue collar jobs, which allowed me to start investing in real estate before most of my peers had finished college.I would definitely recommend getting your real estate license ASAP since you've already said that interests you, and it's relatively cheap and easy.  

So professions where field is growing, money can be 6 figures or more in early to mid career years, and student debt tops out at say 40,000 all in it might make sense.Some students are racking up 60k to 100k in debt for a 50k job where the student loan debt in most cases cannot be eliminated in a bankruptcy!       

I was racked with guilt that I had committed to do something and wasn’t able to execute in the way I had promised.