That being said, I'm always an advocate for paying for mentorship to fast track your goals. 

Withoutknowing the details I can not suggest which would be right to add on.Several you should pay attention to are:- Ordinance & Law: Provides additional building coverage to deal with rebuilding costIncreases due to changes in Zoning or Building laws- Personal Injury Liability: Libel, defamation of character, wrongful imprisonment, etc.

We will be paying nearly $50,000/year in property insurance.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

One thing to think about are the tax implications of being a Canadian paying US taxes.

Currently own three properties but looking to make my first sale.

If you can get all the bedbug containing furniture out of the place and it will sit for awhile (or let it sit while the other repairs are done) you may be able to avoid some cost, but if you want to get a paying tenant in sooner rather than later you will want to bite the bullet and get it well done.

Landlord will promptly respond to Tenant request for repairs but will not be monetarily responsible for tenant disruptions or inconveniences during habitable times of repairs or tenant/guest injuries incurred in or around obvious areas of maintenance, repairs, or construction.We are more converned about them expecting us to pay for their losses rather than getting recouped for damages to our property. 

OMG, please do  NOT take money out of your 401K to pay off a mortgage, especially not for a rental. 

However, value add with a sale is not as implacted by rates.