My recently departed tenant's deposit was not enough to cover all the repairs (repairs NOT due to normal wear and tear).

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620, many blemishes, but should have no evictions in last 2 years.

I am trying to figure out that I have an appropriate insurance to cover the property. 

Not sure if it covers your area or not, but it's a good start even if it doesn't.Find out if your area does them in person or online. 

While I would love to keep it for just us, having rentals to cover the full cost of carrying the property has been great.

I'm guessing that it will be something like 10% to 20% but definitely not 40%.Do you mind me asking how that works, is there a correlation with how they value the property with how much the town needs to cover their budget?

I'm still not 100% what the advantages to that are anyways, even on a 2-4 units but I still have a lot to learn.So what percentage would you tack on to your fund raising to cover taxes, insurance, and upgrades?

I would have this tenant refer back to the lease that they signed for what is covered and what is not covered. 

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

There are some great groups on Facebook that cover Kentucky real estate investment.