You will need to find a good agent to walk through the property, and send you videos (One that you can trust)Get a solid inspection, identify contractors that will give you bids for any big-ticket items prior to you hitting contingency dates. 

Yeah - theres a really good youtube video that covers these questions(Sb9 Yotubue Video): 

I've been trying to read articles and watch videos to familiarize myself but lack practical knowledge for obvious reason.

One video on real estate (Biggerpockets) led me to spend countless hours researching real estate.

Investing into high ROI assets both inside and outside of retirement accounts is the ideal situation, in my opinion.

I hope it will give me more motivation and knowledge than just rewatching all the YouTube videos.

Ideally it would be free, and would allow multiple categories so I could separate my two business, healthcare, and personal. 

IE for me I want low equity, ideally under water must sell and I offer to take over their mortgage payments.  

Then when you get a video walk through of the property, see which items need to be replaced and you will have a list of costs in the area. 

I’d like to invest $100k total so ideally I need to borrow $80k.