I think it’s a more recent consideration (maybe in the past decade or so based on my digging / anecdotal feedback) and perhaps some of you that have been in the business longer and simply renewing old policies may be getting a pass.  

Is it best to simply increase rent by a fixed amount (e.g., $700) to cover this, or are there other strategies for handling utilities in this situation?

To intentionally reduce the leverage more than required is a foreign concept to me especially in the San Diego market.  

If you do decide to help them out and rent continues to be late simply have a talk wiht them and remind them that rent helps pay your bills and since you did them a solid ask for the same in return.  

However, in the City of Chicago and some other areas, the Tenant may have a right to cure the violation and stay.Thirty Day Notice If the Tenant is on a month-to-month lease or an oral lease, the landlord can terminate the lease for any or no reason by simply giving a 30 Day Notice.

We had to schedule another hearing, but when the tenants failed to attend, the court simply scheduled another opportunity for them.

In my experience, it is worth simply reaching out to your realtor first. 

If I were new I would simply stick to areas close to where I live.

Hopefully you can state simply (and truthfully)  at the end of the showing that you have other interested parties to whom you are showing the property and will let them know in due course.  

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.