We took an Ag zoning to Commercial then allowed a Special Use to Self Storage which is Industrial. 

Currently I'm looking for some kind of methodology, software or app, that I can use to manage the properties, which will allow for another family member to step in to my role relatively seamlessly if I were to pass in the future.

Investors allow them to help because they are local but the truth is that they have no idea how to manage a rehab.

In decades past, carriers were allowing people to carrier lower limits of insurance on their properties. 

One word of caution: the court orders typically allow repairs to make a home habitable, i.e. rent-ready, but not cosmetic or similar non-essential repairs, like upgrades or additions.

To get to the ARV of $250,000 , I am assuming as follow:Because you spent $15,000 in renovation, I am assuming you increased the Initial value of the property at 30,000 bringing it at $230,000Add a 8.69% home appreciation for one year $20,000Estimated Home Value After 1 Year:$250,000Refinancing Breakdown:New Home Value (Post-Appreciation): $250,000 New Mortgage Amount (80% LTV): $200,000 Existing Mortgage Balance after 12 months: -$158,035 Assuming 3 Months Interest Penalty for Breaking Existing Mortgage: - $2371Total Cash Pulled Out: $39,594, allowing you to recover to pay a portion of your initial investment of $63,548, leaving $ $24,015 in the deal.Many new investors mistakenly believe the BRRRR strategy ends after the cash-out.

Now Wyoming is interesting as it is a state that allows you to hide partners of an llc from the public. 

I applied for a HELOC and when they ran the title it came up that the 8k grant is actually a second "soft" lien against my property that will go away after 5 years which prevents this bank from allowing me to have a HELOC.

This is the best way to get good at analyzing deals and will allow you to quickly have a good idea about how a deal will work.

Debt service loans typically max out at 75% LTV for cash out refinances, but some lenders allow 80%.