My fiancé and I are both new to real estate. We’re honestly still in a research phase. I am more interested in wholesale but he has expressed an interest in commercial real estate. I’d just like to know how one gets i...

He's only bringing in $3.60 per year per square foot in rent which is WAY low for most every market I have ever looked at. 

Insurance, utilities, management fees, the cost to turn, how long it takes to turn, the cost to advertise, which ads work, foot traffic, closing ratios, trailing 12 months of operation, and then you need to know and have relationships with the top 3 controlling brokers in the market to find the best apartment stock within.Look, I am not trying to scare you here, but there are so many courses out there suggesting real estate is easy when, in truth, there is a lot to know.

We're in a rural, resort area so foot traffic is still a real source of leads for us, especially during the tourism season. 

Gave arbitrary "values" per square foot to come up with his selling price. 

We use the sq foot calculation.

Any recommendations on insurance agents and general rules for average rate per sq foot.

I did a quick look at some of the recently sold condos in her building (Same sq foot and # of bed/baths) and they've sold for about 15-20k more than what she paid for hers back in 2015 so it might make sense to sell now and use that extra cash for a place in a better cash flowing area like you suggested.

Since this will be the very first purchase and the crux to the start of our BRRRR venture we want to make sure we start it on the right foot.

You relet the space using a broker (which you need for this) at $20/foot, NNN.