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All Forum Posts by: Kevin Pillow

Kevin Pillow has started 2 posts and replied 130 times.

Post: STR Co-hosting Regulations

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Luke Carl:

Co-host is what wholesaling is to a real estate agent

just get your licenses and be a property manager 

But you don’t really want to do this. You just have green light syndrome. Remember how I taught you it happens to everyone?

Save your pennies and focus on the next deal. Otherwise you’re just creating another job. 

The whole point of real estate is freedom. Owning the asset. There are better ways to make down payment money than trying to compete with vacasa. 

It’s like buying a mac and being so obsessed with it that you decide to build your own computer. That’s a big old hill in front of you. 


 This is such a great point on the reason many of get into real estate. 

Post: Pensacola, agent needed cash ready!

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165

@Caleb Drake Is one of the top go-to investor agents in that area. He just finished doing a few awesome flips himself so he is definitely someone you want to connect with.

Post: Purchase Luxury STR or multiple mid level STR

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Nick M.:

Invest in STR data for the area you're considering making an investment. I use PriceLabs to price my STRs. Their market dashboards are pretty cheap and have an incredible amount of information. Plus they have plenty of training videos to help learn how to use them. They periodically host live Zoom training sessions as well. You can also schedule a call with their tech support for specific information.

You can drill down into how many bedrooms and what amenities make a difference on rates and occupancy for your specific area. Then you'll have a list of the amenities your house needs when you buy or that you need to add after purchase. You'll be able to get a rough idea of how much adding a specific amenity will add to your revenue. It's not exact but it's better than gut feeling.

I've also used AirDNA but their site doesn't seem as user friendly or have as many data points. And definitely not as much online training.

Good luck!

Shhhh or you will let the cat out of the bag! This is one of my edges over many other agents in the area when I work with STR investors coming into our market. We can see the break out for how much saturation there is by bedrooms and the median price point by bedroom. I think thats a huge value add when you want to leverage data to select the best types of properties. Especially now when everyone is jumping in vacation STRs.

Post: When to consider purchasing vacation STR

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165

There are pro's and con's to buying in the off season vs the on season depending on the condition of the property. Here are some observations I've seen clients have to deal with when buying in the off season.  

1. Easier to get into properties for showings/inspections/repairs during the contract to close phase.
2. Sellers a bit more flexible on pricing/contingencies. I think it's because many of them want to 1031 into something else. 
3. Don't have to worry about losing out on the most profitable time of the season due to getting a property ready if it is not turnkey.

When clients buy in the on season they can step into a great cashflow situation where they are making profits right away but that usually only works out best when the property is already furnished and is already being used as an STR. A perk of being in a vacation market is many of the properties used as vacation rentals, the sellers are willing to let the furniture convey.

So many choices but @Matt "Roar" Gardner is the one. He has multiple multi family investments throughout the south and runs a syndication. He knows his stuff so you can definitely get some value from talking to him.

Post: Cash on Cash return for STR

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Bruce Woodruff:

I was going to say at least 20%. And don't use AIRDNA, their numbers are usually flawed. Go on VRBO and see what your competition is really getting as far as occupancy and rates.....

I don’t agree that airdna is flawed, it may be a market by market thing but here in the Destin/PCB area they are fairly accurate. 

Post: Looking for PM in STR areas.

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Christopher Brownlee:

I am finding that the PM's have the best feel on what each STR market is looking like and even have a good few leads. Any PM in the south that has a potential STR, I am looking to grow my portfolio in as many different STR markets as I can. I am trying to keep in the sub 225k range and would not like to have to manage the property at all.

Also, looking for a partner on a few deals. Only have cash for 2 deals right now. 


@joshmaier runs one of the best STR PMs in Panama City Beach.

Post: Cash on Cash return for STR

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165

This biggest variable you will need to watch is your acquisition cost. The down payment and closing costs are the main components of the deal acquisition, so if you put 10% your CoC numbers are going to look better than if you put 20% down. That comes at a trade off for that higher CoC return and it is the cashflow amount. If you put less money down and are financing more, your monthly principal & interest payments will be higher and that reduces your cashflow.

The equation for CoC = Cash Flow÷Total Acquisition cost

Total Acquisition costs are made up of:
1. Down Payment
2. Closing Cost

Post: Panama city beach income numbers

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Jamie Hoth:

Thanks! We another unit in Indian Shores near Clearwater and we started looking down there but could not find anything in the price range we had to work with. We eventually were told to go to Panama City and you will get way more bang for your buck. They seemed to be correct.

To add to what you said about "bang for your buck", this is a recent article from AirDNA on the most popular places people visited for 4th of July 2022. The emerald coast had 2 of the top 10 spots, Panama City Beach and Santa Rosa/30A. Here is the link https://www.airdna.co/blog/air...

Post: Panama city beach income numbers

Kevin PillowPosted
  • Realtor
  • Destin, Fl
  • Posts 138
  • Votes 165
Quote from @Jamie Hoth:

I recently closed on a unit in the Shores of Panama a 2 BD/2B it has only been a few months but so far it is going great.


 I think people are in disbelief/skeptical when we tell them how well they can do, especially if they self manage. I'm glad you pulled the trigger!