For insurance, I’d recommend working with a local broker to explore the best rates.

Forget Title insurance. 

First and foremost, I'm in Minneapolis / Saint Paul, so I'd like to know if you have any suggestions for 1) what investor meetups I should attend, and 2) recommendations for building my team (CPA, real estate lawyer, handyman / contractor, insurance broker, and agent (I have one but they don't seem to have much investing experience)).

Pros: Diverse job market, low unemployment, great resilience during recessions, nice appreciation, 1% rule can be hit if you look hard enough, great economy, good schools, Midwest nice.Cons: Extreme weather at times (hot/humid summers, tornadoes/hail, brutal cold in Jan/Feb), high insurance premiums, property taxes also really high.

Personally speaking, from an investment broker and investor standpoint, I feel single family investing is the riskiest in some investment ways in comparison to larger investments due to the fact that it only takes 1 repair or tax/insurance hike to put you under or lose all income.

With fresh paint throughout inside and out, brand-new roof, dual HVAC systems, updated water heater, stainless steel appliances, lighting fixtures, outlets, countertops, and PEX plumbing just to name a few.

You’ll want to make sure the rental income comfortably covers the new mortgage, taxes, insurance, and any maintenance costs.

And STRs really help because you don't have the large dings that long term rentals have - i.e tenants damaging the property to where you have huge make ready costs (the str insurance covers that), no collections or evictions issues. 

I told them I would consider it as I'm hesitant about having this "contractor" do any plumbing on my property.

But there are things you need to consider, like: everyone has to follow house rules to avoid drama, excessive use of kitchen and bathrooms leading to plumbing issues, being on call 24/7 with any problems, etc.