When I click on the 50% rule tab it says cash flow is a little over $100/monthWhen I look at investment over time, it says that I'm losing in the first 5 years. 

You have decades ahead of you to screw up, recover, and try it again. 

Know ahead of time where you want to invest and do what you can to know which real estate agents, attorneys, contractors and property management companies are in those areas so you're not left scrambling for contacts when an opportunity presents itself.

I'm thinking if we can encourage the current tenant to vacate early, we can get a head start on repairs/updates and have it tenant-ready sooner.

Sounds like you are really ahead of the game if you purchased your home in 2010.

I would say if you know the area well enough and/or have a good Realtor (happy to put you in touch with someone) to help you find a good property then go ahead and buy something now.

Maybe you’re way ahead in that than me, but I believe we need to work on ourselves first before anything else.

Your other siblings may have to sign on the loan as well-depends on the entity you get the loan from.Just a heads up -if a family member is moving in, discuss terms and get s signed written lease before they move in.

Ask them ahead of time and that you don't like personal liability. 

We installed a meter ahead of each panel so we could send the tenants a bill.