For example, if an HOA fee is high for the area, I'd hope it would provide at the very least some amenities, but possibly cable and internet as well.Also, do some research and make sure that condos make desirable rentals in your market.

i.e. maintenance, make sure the firestick/cable channels are working, make a shopping list of things needed like laundry soap, coffee etc. 

I would set aside 6 months reserves for electric, water, gas, cable, internet, landscaping, pool maintenance, etc.

We went to change a light fixture and found the old cable to be semi-dry rotted and don’t want to or have the time to pull new cable/we would love to have a professional look at it.

Oh no, you're getting direct mail...must be so hard to throw it out along with all the insurance, cable, coupons you get." 

.$100x200=$20,000; $20,000/12=$1,667Similarly, on the expense side, adding in the additional STR-specific expenses (Cable, WiFi, utilities, etc) and averaging them out for each month can give you a decent expectation of monthly costs.

The area is good compared to others, cable's down in some parts and  non major flood anywhere. 

I refuse to play that game.There are a dozen ways to split a water bill and require tenants to pay it in full each bill period.The same for gas, electric, cable, phone, or anything else.It helps if the lease states the obvious responsibilities along with repercussions when the lease is NOT followed to the letter.This may take an actual attorney to help you write this into your lease, and it may cost to have your attorney effect the discipline required by said lease.Just save that talk saying there is nothing you can do but change toilets, faucets, and make sudden inspections.

Would installing a EVSE with a J1772 connector on the cable provide what is needed?

Cable And InternetFor larger properties, there are certain cable and internet providers that may be willing to provide a hefty payment in exchange for the exclusive rights to offer their services in the community.