My biggest weaknesses are evaluating a residential deal and understanding/exercising the tools used to leverage properties in order to expand one's portfolio.

For tenants with weak financial standing, fixed term leases are not necessarily a good thing.

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.

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

It has worked out for me for the most part.I've also worked with people who are chronically late paying rent.  

The file place was ultra weak with no ability to quickly search the files.

@Steven WiltzI found it to be easier to re-sheet (over) the whole floor with 5/8" rather than try to piece in areas and inevitably have another weak spot somewhere, I guess you have done this for a while though.

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.

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