Skip links

Key West!

I know it’s not Sunday but I will not be available to write a post tomorrow so here it is a day early. The photo for this post is what I am looking at behind my computer right now. The beautiful sun and sky of Key West!  As much as I would like to tell you all this is the great life of a real estate investor, it was the Navy that brought me down here.  Most of you know that I am an instructor pilot at Whiting Field in Milton, FL.  Occasionally, we have the opportunity to fly what we call a cross country to destinations around the US.  It is great training for the students and the instructors as it builds confidence in unfamiliar airspace and airfields.

For this trip, we flew 3 graded events for the student on Friday and we will fly 3 more back home tomorrow (which is why I won’t be writing a blog post then). On the way down we stopped in Adalusia, Alabama for fuel, then went on to Tampa, FL and finally stopped at the Naval Air Station in Key West, FL. My mom is down here in Key West right now so it has been nice catching up with her today.



With real estate always on my mind now, it is different driving around down here than it was years ago when I would come down and go fishing with my college buddies.  I look around and wonder who owns all of these rental properties, hotels, bed and breakfasts, restaurants, commercial buildings, etc… and how much they are raking in every year. I wonder how they acquired the properties and how a yellow letter campaign in Key West would perform.  I’m sure there are a lot of motivated sellers or soon to be motivated sellers here (right?).

There are a ton of properties here that need some serious fixing up!  However, the price points on these places are insane.  I don’t think I could buy a hot dog cart down here for less than $200k.  But, it is nice to look around and wonder, isn’t it?

I know I just rambled on but I don’t have a ton to talk about this weekend anyway.  Here are some updates to what we are doing.

We have 2 houses on the market right now that will hopefully go under contract soon.  The house in Navarre is almost done and it will be going on the market soon.  The only thing left in there is the pool cleanup, counter tops, appliances, and the final punch list items. The Gulf Breeze house is coming along nicely, I’m looking forward to going to look at that one next week.  We have one almost finished in Milton and another one just getting started in Milton.  Lastly, the house in Mobile is coming along and we decided to pull off the vinyl siding and go with Hardi Board.  I really think that will boost the resale value of the home.

We got another property under contract yesterday.  On top of that, we have 3 houses closing on Friday of next week!  Things are moving along well and the team is getting bigger, I will update you on our newest addition in an upcoming post.

With all of these projects, I am looking for more partners to join the team.  So, if you have ever considered being actively or passively involved in a real estate investment reach out to me.  I would love to take some time out and talk to you about how we could put together something that would be mutually beneficial and give you a safe, consistent return!

For those of you who are local to the Pensacola area, I have started a meet up group that meets on the first Monday of each month at 6pm.  It is at Oops Alley in Pace on Highway 90, and this month we will be meeting in the conference room.  There is no teaching or up selling, this group is entirely about networking with other ACTIVE real estate investors in the area.  So, I hope to see you out there this Monday, May 2nd at 6pm.

I am also going to be speaking at a friends meet up group on Tuesday, May 3rd at 9am.  He has a get together every Tuesday morning at the IHOP on Highway 29 in Pensacola.  I will be speaking about how to make killer returns using your IRA and/or 401k in Real Estate.  This is near and dear to me because I wish someone told me about this when I started investing in my IRA over 20 years ago!  It would be over twice the size it is now, I’m sure of it.

If you don’t live in the area and want to hear more about Self Directed IRAs and 401Ks, email me at or give me a call at 850-483-1761 and we can talk more about them.

Thanks for reading and I’ll see you all next week, if I decide to leave Key West tomorrow!

Leave a comment




  1. Hey Bill,

    Listened to you on a podcast the other day. Just want to say it’s great to see how successful you have been, especially with the balance of your military obligation and family. You are a real inspiration. From one vet to another, thank you for your service and thank you for sharing your experiences.

    1. Thanks Chris, I appreciate the kind words! Thank you for your service as well, if you ever make it to Pensacola make sure you look me up.

  2. I just found your blog from a link in a post you made on BiggerPockets. I have enjoyed readying through your blog and you have a gift for keeping it intriguing and informing at the same time. It really reminds me of J Scott’s blog a lot but with your own taste. Just wanted to say thanks and that I hope you keep killing it. Really bothers me that I don’t live near Pensacola (I am about 4 hours north of you in AL) or I would have applied to work with you in a heartbeat given my situation. Take care and look forward to reading more. I’m going to give Jerry Padilla a call on Monday since my 1st rental seasons on June 23rd and need to refi so I can repeat the process. I’ll tell him that I found him on your blog. Thanks again.

    1. Donnie,
      Thanks for the comment. I’m glad you enjoyed reading this and it’s always nice to hear people are following it. I have been slacking the last week while I was on vacation so I apologize it took me so long to respond. It’s going to be time to expand in the next year or so, maybe your market will be a good place to do some wholesaling? Keep in touch!