As additional perspective, I'd prefer to invest in or near my local market (Raleigh, NC), where is VERY tough and competitive to find multi-families!

I would prefer not to do that if possible, because I don't want to expose myself during this brief vulnerable period without protection, but I also don't want to break any laws or LLC shields if this process is not handled correctly.What are your thoughts?

Any ideas on how I can find a teardown preferably off market?

There are tons available, usually free to the Landlord, and it's just a matter of trying several and determining which one you prefer.

If there is a potential court case, my high preference is to not be in court. 

Liability CoverageThe liability section of insurance is fairly similar across the entire country.  100k is the minimum required on a policy, 300k is recommended, and 500k is preferred. 

That is up to your preference as an investor and your comfort level with whom you are working with. 

I prefer to pay $6k a month and complain, while preparing for purchase instead of buying a headache at $4-5k and needing cash for assessments, etc.....Rent first, then buy.

I’m currently paying down debt by this summer and should have saved for a relatively small deposit by EOY 2019.Here is my current position.Purchased 1st property as a USDA in MauiUSDA Ln: $400kMortgage: $2202Consumer Debt: $0 (06/2019)Owe Aprx: $385,000Home Value: $500kIncome: $74k yrlyDown payment: $23k (12/2019)720 Credit score Im looking to purchase something small, preferably in a wooded mountain area (ideal for short term rental) but open to anything affordable.Right now I have my short term goals set out but been wracking my brain trying to figure out the next best possible approach to REI.Any help or advice would be GREATLY appreciated!

It'll be a personal preference choice.