Regarding your GF's grandmother's home, you should consider setting up a recorded legal agreement with an attorney in the matter that benefits everyone that is part of the deal.

Buy and hold typically provides the best tax benefit if you are either a RE pro for tax purposes, or your AGI is under $100k. 

In a case like that I do not see the benefit of changing a roof that still has life left in it.

I would buy stock following the value investing strategy followed by the Warren Buffet etc.Real Estate has that benefit of control over the assetSO i guess both would do, its just a question of weighting -95% real estate-5% stocks for example

Brent, this makes sense, should be a benefit.

@Zach JonesYou may want to see if it makes sense to create a QOF to invest in the property.There are some considerations for this to work - Is the triplex in a QOZ(qualified Opportunity Zone) and are there significant repairs that need to be done to the house.If you were to sell the Stock / Crypto - are the assets atleast long-term where you benefit from reduced tax rates?

There is also the benefit of having an extra layer of anonymity that comes from having the LLC own your properties.

@Gregory Schwartz brings about a great point when he stated working for others and learning systems in place could benefit you in the long run.

I am also talking to my CPA of possible tax benefits for the year for renting (versus selling). 

It's better to have it "done right" rather than trying to cheap out.You know Bigger Pockets also has a benefit to us pro members in the form of a contracts section if you're feeling brave :)Keep us posted please.