One thing that I think you could do that will partially meet your goal is to invest through a SD-Roth IRA in an investment property, have that property generate enough cash flow to cover your initial contribution (and be financially self sufficient with adequate reserves in place) and at a later date withdrawal funds equal but not exceeding your contribution amount.

Is there a primer anywhere on how to properly limit my liability or how to make sure that I have adequate insurance as a landlord? 

Check out FHA and 203k loans, HUD properties, and things of that nature.

We are releasing this toolkit well in advance of the effective date to help the mortgage industry come into compliance with the new rules,” said CFPB Director Richard Cordray.The toolkit, which can be found here, provides a step-by-step guide to help consumers understand the nature and costs of real estate settlement services, define what affordable means to them and find their best mortgage.Complete Article from HousingWire

If you feel that $40k to $80k is a lot of money for a car, you have not adequately prepared yourself for life in Los Angeles

I am conservative by nature although many think I take to many risks (again relative term).So where do you invest outside your home state and why?

Just the nature of small town workers not all are professionalized:  bank account, newer smart phone, have cash to wait for a check to clear etc.A contractor suggested I use green dot prepaid card to pay him. 

Sometimes it is hard to garner things from posts because of the terms being mixed up or misused.That said, OP (brother et all) purchased an asset that naturally flows into real property at auction.  

These transactions are much more complex in nature and I have a specific skillset which adds a lot of value.There are potential clients that believe they know it all and everyone else has limited value.

@Zach SchwarzmillerOne flooring choice for bathrooms and laundry not mentioned here is linoleum {I am referring to real linoleum here and not the incorrect use of the noun in reference to sheet vinyl}It's available in a variety of colours/patterns, is organic and naturally anti-bacterial, and lasts well.