Even I get weak and think of all the ways I could help out siblings with what I know, etc.

Our one weakness is that we do not really have any inventor of larger multi-unit properties 20+, those almost dont exist. 

That is one of my weaknesses as well, which is why it is such a current focus for me.Feel free to reach out anytime..by the way I read the whole post!

Analyze your strengths and weakness and then pick a strategy and go with it.. worst case scenario is it doesn't work as expected then just try a new strategy. 

I’ve done some surface level research and know that you can pay third-party services, but wondering if I can outright cancel due to medical reasons for my dad (cancer) who is too weak to travel.

You need to look at your weakness as a strength because it really is a strength.  

I was considering purchasing a duplex or multi-family home, but I'm a first time RE investor and I'm worried about the debt, being saddled with repairs, dealing with tenants, and the worry of weak cash flow.

If a weak deal comes along pass.

James or Nick may have more insight into this aspect, but you might be able to have another deal totally unrelated to the subject property.Getting personally involved with people in distress was a weakness of mine, you can't go too far.

I'll toot my own horn (weakly).