All Forum Posts by: Chuck Masters
Chuck Masters has started 9 posts and replied 92 times.
Post: Looking for towns that are mainly tourist driven to buy an STR

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
@Ashley Zhang I have a local property manager on the ground in Kissimmee that handles the cleanings, pool care, pest control, maintenance and has a toll free number for the guests to call in case of an emergency. I keep the villa rented via VRBO and keep my calendar synced with my property manager. Many property managers will also coordinated keeping your villa rented but I preferred to do it myself. I should also mention I travel to the area several times a year and stay in my villa to vacation and to check on how things are running.
Post: Looking for towns that are mainly tourist driven to buy an STR

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
Check out the Kissimmee and Four Corners areas near Disney World for your next STR. Just make sure the HOA is STR friendly.
Post: Registering your guests

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
You could create a form and then use DocuSign or SignNow to have your guests digitally fill out the form at the same time as you have them sign a contract for your terms and conditions and also provide a government ID.
Post: Installed a Camera at VR Home

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
@Luke Carl cool idea. I’m not familiar with iGMS, what is this? I’ve been looking at virtual concierge service that works with an echo or home device to do something familiar.
Post: Installed a Camera at VR Home

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
I'm using the Arlo Pro 2 camera mounted in a tree facing the front of the house. I'm also using the Arlo solar panel to keep it charged. I turned off the notifications because it was driving me a little crazy. I like to check to see when the guests have arrived the first time so I can follow up with a welcome e-mail and ask if they have found everything to their satisfaction.
Post: Short term rentals near Disney.

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
Post: Commercial Liability Insurance

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
@Jared Newsom I would normally agree with you but the vacation rental is the wild card in this equation. A vacation rental is the one circumstances that wouldn't be covered with just an umbrella policy. When I first started looking into insurance I was looking for an umbrella policy and agents here on BP and in Florida both said that an umbrella policy would not be adequate. There are two companies CBIZ and Proper that specialize in this liability insurance but because they are small and Florida is a specialized state for insurance the rates after adding wind coverage are 3 times what a normal policy costs.
I have contacted many independent agents in Florida and I was amazed at how many agents that know very little about how to insure a vacation rental. I learned most of what I know from folks here on BP.
My question was what am I missing by dropping the liability on the landlord policies and having only the commercial liability policy.
Post: Commercial Liability Insurance

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
I own 2 properties in Florida. One is a long term rental and the other is a vacation rental (short term rental) and I live in Maryland. Each property is currently held in my personal name and each is insured by its own landlord policy. After spending lots of time reading many posts here on BP regarding insurance, I've decided to go with an additional Commercial Liability policy to supplement the landlord policies to cover both properties.
Since the liability insurance is with a different carrier different than the landlord policies I was told I will have to remove the liability insurance from the homeowners policies so the new commercial policy (3 million) will cover any liability.
In general, am I giving up any liability coverage from the landlord policy that may not be covered by the commercial liability policy when I terminate that coverage?
Just trying to make sure I'm not missing something.
Post: Insuring a Short Term Rental

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
I appreciate all of the great ideas. I'm surprised none of the insurance agents on BP haven't weighed in on this discussion. Several folks alluded to an umbrella policy or premises liability policy but they don't really cover STR under 30 day stays adequately. One scenario that is not covered say you allow pets in your STR and the STR guest is out walking their dog and that dog bites a neighbors child enough to warrant some sort of medical care. Now the parents of the child want to sue cause that is what everyone does these days so they sue the STR guest, if they can find them, but guess what they can find me and I'm the deep pocket investor (which I'm not) so they sue me cause without me that dog would have never been in the neighborhood to bite the child.
On premises liability only cover what happens on the property the biting of the child if it happens down the street off property this is not covered. While the personal umbrella policy may cover my issue has been I live in one state and the STR is in another and I have not found anyone to sell me an umbrella policy without trying to sell me coverage I don't need or want.
I assume a commercial liability policy is needed since it is a business but I had my agent tell me since it was titled in my name I couldn't get a commercial policy. Time for a new agent.....
If any STR owners operating in Florida have some referrals to insurance agents/brokers that can help me out, let me know.
Post: Insuring a Short Term Rental

- Investor
- Bel Air, MD
- Posts 95
- Votes 57
I read on the forums all the time if you own a rental, in this case my example is a vacation rental, that is titled in your own name all you need is a landlord policy and an umbrella policy to be covered. While this sounds fine on paper and others may be doing this I can't seem to find the right insurance. I live in Maryland and my vacation rental is in Florida a state where many insurance companies may not care to partake in.
I have a landlord policy on my VR but when I asked my agent about an umbrella policy he says I must include all of my personal assets back in Maryland , cars, homes, etc in the policy to get coverage in Florida. I already have an umbrella coverage on my personal assets and I just want it for my VR in Florida and he says all he can offer me is an additional premises liability policy to my existing policy. While this is fine for a typical long term rental this is inadequate coverage for a VR.
Today I got a quote from Prosper a company that specializes in VR insurance, but when you add wind coverage aka hurricane coverage the policy is 3 times my current landlord policy with wind coverage!
So what is the correct way to insure my VR? Also it's probably time for a new agent.