Start with BiggerPockets Ultimate Beginners Guide (free).

Really anyone on your team should be an investor if possible as then they will understand exactly what you are looking to do, and they can guide you through all the issues as they come up. 

I do, however, have a large portfolio of SF homes and understand the work that is involved and the hidden expenses that no one talks about. https://www.biggerpockets.com/member-blogs/10145/83067-limited-partner-s-guide-to-investing-in-the-right-dealhttps://www.biggerpockets.com/member-blogs/10145/73373-opm-how-to-syndicate-with-successhttps://www.biggerpockets.com/member-blogs/10145/72118-syndication-the-ins-and-outs-of-real-estate-syndication

A lot of people skip this but it's a huge advantage if you can work through it.Every Landlord's Tax Deduction Guide- is a really good book on taxes and setting yourself up for success as a landlord.

My questions may seem simple but I fully understand its complexity: what is the best way to make this happen, what direction do you recommend for the refi cash out, what strategy to utilize to help guide me on this journey of educating myself and building confidence through working in notes and multifamily acquisition and ownership?

Here is an article that I wrote that my help:https://www.biggerpockets.com/member-blogs/10145/83067-limited-partner-s-guide-to-investing-in-the-right-deal

If the tenant were pleading absolute poverty yet DID get their stimulus check, that's an outright lie.

Bonus if it can be turned into an educational how-to guide.The resident can either pay out of pocket for any work needing to be done, or they can let the GNA cover it in exchange for direct principal payments off the original market price purchase.Make a simple guide to what needs to be done on a regular basis, and establish a plan for what the resident can handle, vs what the GNA provides.Create synergy with kids and grandkids to accomplish common/ regular tasks.Opportunity for daycare/ day camp, or even homeschool type services.Opportunity for future continued business partners to take over living on the residence.Preferred scenario, resident pays for material and professional labor, and the GNA provides cheaper labor for easy tasks etc.Residents may pay part of the labor cost, but ideally if the GNA has cash to pay internal employees, then those costs get applied as principal payments.Explore options that let GNA employees trade time for ownership of that specific property, instead of traditional pay, or use it as an overtime bonus.Find ways to incorporate local artists and craftsmen, and make unique projects that incorporate the story of the house as told by the resident.

Regardless of the offers they have a guide line they have to follow.

It's very difficult due the nature and age and deferred maintenance on most of the properties you'll be looking at.Do your homework, take the online course under the education tag, listen to many of the podcasts, read many of the blog posts and guides, buy recommended books and learn more, ask questions in the forums, get as much value out of the time you spend on BiggerPockets as you can.