However, now I wonder if it might be a good idea to set up the property management company first to take on local clients and propel us into the space faster.

just because you bought a BRRRR or a turnkey doesn't mean you'll appreciate slower or faster. 

Vrbo has free price automation software.I use Excel for book keeping.I don't pay for any third party software, not really needed on 1 or 2 properties.I charge a little extra for cleaning fee than actual cleaning costs.

A BRRRR strategy or house hacking with a duplex can maximize your returns.Consider leveraging financing to acquire multiple properties, which spreads risk and scales your portfolio faster.

You don’t think you can charge $2/day more with appliances?

I charge two months security deposit (roughly $3,850) per unit and have only once needed to deduct for anything other than a cleaning fee.

It costs me $50/ PER MONTH and I can use it as a hotspot at no additional charge. 

Some common names you'll see thrown around a lot: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend you search for each of those apps online and see what they offer, how much they charge, etc.

From what I've read, some electric providers might not charge for the new service upgrade itself, but adding the meters, connecting the upgraded service and adding/updating panels would require an electrician, which would incur costs.If anyone has experience with this type of electrical service upgrade, particularly in Chicago, I would appreciate your advice and any information on costs and the process involved. 

That will be an experience in itself and should get people down to Playa and Tulum faster and less stressful than driving.