People sometimes make bad decisions in life and you have to decide whether it is forgivable or not.

Edit: And taking 10-20% equity on a deal like this with an experienced investor might be completely worthwhile and life changing to be clear. 

2-4 paid off properties in great areas with minimal headache is likely life changing for most people who don't overspend monthly. 

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

At the end of the day, that is life however to Stuart's point, you may want to consider investing in better areas where this does not occur normally if this is an unsettling occurance for you. 

I recently had a buyers agent tell me (at my house) my heat pump was 20 years old and was at the end of its life and needs replacing . 

Ask anyone with investment property and they'll tell you it's not passive.I earn enough from investments that I could be financially free for life, assuming nothing major happens.

Getting started a little later in life than some, but that's ok.

What real-life clients of theirs did you talk to? 

A set of new machines can easily run you 300-400k if these are all end of life.