Do you have a contractor that you would recommend for Toledo?

YES you 100% need PM. ( I know most happy to recommend) YES you need insurance.

I've also talked to recommended Realtors in each city. 

I would give her notice of termination and get rid of her.I also recommend you set some standards and stick to them.

I would recommend you read Profit First. 

Do you recommend that I start the process when the current tenant's lease ends, or when the tenant is still in the property?

Selling your Triplex-- I would recommend doing an a1031 it's a bunch of money for you and I'm certain that you will be able to find a property in East Bay ( Hayward, Oakland, Berkley, etc) to match what you're looking in terms of returns/cashflow.

I would recommend only using a short or mid-term rental house hack for a 2-4 unit property or a house with a detached ADU for your security and the comfort of the guests, which will make it more profitable.

My recommendations would be definitely try to get another job and save up as much money as you can.

I will always recommend using someone that comes as a referral from another person that has used that company/person.