Then they add or subtract for location, age, size, etc. 

Those you could see yourself when you looked at the house . put on the 5 year list .The deck , without seeing pictures is hard to tell , could be age , could be poor design , may or may not be expensive All in all that report wouldnt scare me at all ,  Its an older house , it will be constant maintenance .

You're paying for a brand new build (with high build prices) but people will associate the age/condition with the existing old/leaky structure.

House that's been owned for ages, same owner or tenant for years.

This post has aged well. 5 years ago it was still easy to buy in Milwaukee, even in great areas.

The owner will want shorter term as possible due to his age. 

For instance, they're opposites in terms of liquidity, physicality, age of the business model, volatility, etc., etc.  ...and, my impression is that they're also opposites in terms of the mindsets of the investors (e.g.; many RE investors have comparatively longer time horizons, and I would assume that most RE investors have a lower tolerance for risk).I'm a RE investor, and don't have any crypto, but I have plenty of friends who hold a lot of crypto, and we've discussed crypto endlessly...At the risk of sounding like a luddite, even after years of discussions and reading countless articles, I still don't feel like I have a good understanding of crypto.  ...and frankly, I'm skeptical of people who claim to have a thorough understanding of it (yet, there are no shortage of self-proclaimed "experts" who describe crypto with the confidence of someone predicting a sunrise!)

It really depends on your goals, experience with REI, and level of PM you want to handle at that age. 

No one under age 50.Congratulations on saving,  it can really work out well, Real Estate is very stable. 

He said your dad comes from a different age where things were maintained differently and that I need to make a move if I want something.