Hi @James KimLot's of variables to consider however I suggest working with an insurance broker that has access to different coverage options and carriers for your properties.

what’s the major carrier of bond money ?

You'll want to pay attention to the proposals/quotes you'll be receiving though, because some carriers will do a separate higher wind/hail deductible.

@Jon-Michael ClarkIt's likely you have reached your threshold with the carrier you are currently with.

There are different types of dwelling coverage that an insurance carrier can provide its customers.

With respect to the actual personal injury lawsuit, if one is initiated, your insurance carrier should be providing you representation at no cost as part of your policy, but yes, they will only likely pay up to your policy limits and the plaintiff can come after your assets for any verdicts over the policy limits.

Four months into the policy I receive an endorsement letter and invoice from my Insurance agent that says after the carrier did an external inspection of the property they needed to increase the dwelling coverage by $90k to reflect the replacement cost of the property in today's market.  

A personal umbrella requires auto coverage unless you don't own a car (because that is where your greatest risk exposure is) and therefore in most cases your auto carrier will offer a multi policy discount.  

A flipper is indeed a real estate investor, but they have additional exposures that align them more with a construction company in the eyes of many insurance carriers.

Would any insurance carrier have this?