There is around 500k equity in the property. 150k-200k would get the property fully rented at top dollar with desirable tenants. 100k would get it to where I can rent all the units back out at fair reasonable market rents.

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

It's more important than doing individual property analysis, because when you do a proper market analysis, you are analyzing ALL of the properties in any market(s) at the same time.Now, one of the analysis "pitfalls" is not understanding what defines a market, or more importantly, a Micro-market.Another problem is focusing on one strategy, and trying to fit each market/property. 

Contact the zoning department and see if you can get the property rezoned as a duplex.

Until now I've focused on distressed single-family and small multi-family properties for rehab into rentals (BRRRR).

Would you eventually scale down to fewer properties with higher cash flow, or continue holding indefinitely?

I've handed off my LTR to a separate PM and they want to be named on a general public insurance policy for the unit, but truth be told, I feel like I need a solid umbrella policy to cover the MTR and any claims against myself and husband as the owners of the property.

We currently have 3 properties.

Financing your second property can be tricky since lenders may only count 75% of rental income toward your debt-to-income ratio, so get pre-approved early.

We manage a property that was having drain field issues for awhile, got estimates and had the owner approve one of the vendors.