I have been a devoted follower of this blog for over 5 years, and I distinctly remember a post from Mike four years ago in which he stated: "I have been investing for a few years in the Riviera Maya and was recently presented with a private condo deal in Tulum.

I think that is a very important distinction.

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

It doesn't matter if you deduct it on schedule C as a management expense, or schedule A as a contribution, the result is exactly the same.Perhaps a distinction you're missing/misstating: "Meant Schedule A, and the Charitable Contribution is deducted from the Tax you owe, plain and simple"Charitable contributions are deducted from your taxable Income, dollar for dollar. 

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.

@David Friedman it’s funny how these threads age… I ended up scaling my flips to a point where it just makes more sense to get into a strategy that takes advantage of the economies of scale.

And if not, no worries :)Not to age myself but i started in  1975  LOL..