I bought the pair from a used appliance place three years ago for $250 total.

I do think that getting out there and meeting people  will get you to a point but you're also going to want to pair yourself with an investor friendly agent that can also take a deep dive with you and what your goals are.

The impact of this question is the ability to add Canadian addresses, noting investments in different currencies, etc. 

Your hundred dollar buy less today than 2 years ago- most asset will have long appreciation anyway especially real estate property as way to hedge inflation and possible currency devaluation- cash flow is always good especially if property located in appreciating market

Are we looking at REITs, tech stocks, muni bonds, commodities, currencies etc.?  

By simply knowing your preferences and using our data correctly, we can easily begin pairing you with content and people that are relevant. 

I hadn't paid state income tax since leaving MN 25 years ago.This year I sold a pair of cabins I had held since leaving town for my parents to enjoy.I purchased for $50k and sold for $250k.

Most importantly pair up with a bank that will help you structure these things to maximize every position you can.

Oh wait - you mean real estate investors should learn a lesson about how blindly following advice to invest in crypto currencies worked out?

I want to do it again, but I am trying to stop spending my cash flows on the investments so I can buy a new pair of shoes.