New from Chicago Suburbs or Daytona Beach, Florida

14 Replies

My name is Shane, and I'm currently living in Grayslake, IL which is a far north Chicago suburb.  I own 2 rental properties, a former primary home of ours, a 3/2.5 in Round Lake, IL and a condo in Oak Park, IL.

I say that I'm also from Daytona Beach because my wife and I are thinking about relocating to the Daytona Beach or Jacksonville area.  So I'm maybe looking for some advice on that as well. The property taxes in our current area are sky high, and I feel like our money would go much farther down in FL.

I want to continue to purchase buy and hold properties (or fix and flip depending on the deal) to eventually quit a traditional 9-5.  We have a 4 year old son, and twins on the way, so I'm probably a long way from quitting the 9-5, but a guy can dream!

I miss Chicago, but gotta tell you; as a recent Florida transplant, there IS something to be said about wearing flippy-floppies in the middle of February!

Daytona Beach should be a great market; the further north you go from Miami/ Ft. Lauderdale the more down to earth the prices get. 


Hi Shane, welcome! I used to live in Grayslake and now rent the house. Taxes are dumb .. I couldnt sell it for more than $315k and I am paying $13k in annual taxes. No kids in the school district either. Best of luck if you relocate.

@Shane Huckstadt

Welcome to Bigger Pockets. I'm looking to invest in vocation rentals in Florida.

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Originally posted by @Shane Huckstadt :

  We have a 4 year old son, and twins on the way, so I'm probably a long way from quitting the 9-5, but a guy can dream!

 hahahha and dream you shall. Dreams is what wakes us all up every day. The dream of the goal. That day... oh that special day. Congratulations twins!!!! YOWZERS!!!

Shane, I live in Wheeling, IL which is not too far from you. You should consider looking for SFH that are in pre-foreclosure and REO in C areas like Zion, Winthrop Harbor, Waukegan and North Chicago. Just a suggestion and now would be a great time to look as sales and interest in these types of properties are slowing down at this time of year. There certainly are some undervalued properties in these are for flipping or buy and hold.

Hey @Shane Huckstadt , welcome to BP!

I have to second @Ken Badziak , I'm a transplant from the Pacific Northwest (Portland, OR), and while I miss it, there's a lot to be said for having a natural tan in November.

@Renea Steward gives some great advice. Engaging consistently on BP is a great way to learn, connect with other like minded people and ultimately achieve your REI goals.

Both Daytona Beach and Jacksonville are great buy and hold markets, and cost of living here is pretty darn low.

I'm an active investor/agent in Orlando, so feel free to reach out anytime.

I wish you and your family all the best Shane!

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