Multi-family homes provide more cash flow, risk reduction, and economies of scale, but they need more capital and may have higher turnover.

I’m looking as well.

You could do this if it debt covers, but it usually makes more sense to do a refinance as it will be more stable and provide better rates

Does anyone know an agent/manager who can provide insights on the tenant screening process and possibly guide us in the right direction?

I’d love to get together with active wholesalers in the area to share each other value we could provide each other.

Look into a vacation home loan as well if you own primary. 

There are some special assessments coming up, and I've heard that some of the neighbors have been dropped by their home insurance providers and are struggling to find affordable home insurance in SD. 

Your experience in leadership and crisis management will definitely serve you well in this field.

My wife and I plan on buying another property at the end of this year and will probably move that property into the LLC or Trust as well.

I have tenants pay it directly with the utility provider when possible.