Moving from Chicago IL to Orlando FL to follow my dreams

[Sean Schwebel]

Hello everyone,

*This may be a rather long post and question but please hear me out if you're a credited investor, real estate agent/broker, or financial advisor. Your help could change my life. 

A few months ago I was headed to my regular job when I was suddenly struck by a semi-truck that was going full speed. My car was completely totaled, but thankfully, I wasn't. I’m not sure if you are religious or not, but I believe that God had a true plan for me. It was an exhilarating moment of epiphany. I believe that he was telling me it's time to start following my dreams for real this time. All in. No holding back.

But right now I feel like I'm that kid from High School that loves to play sports, but can never make the team because he isn't big enough, strong enough.. or even good enough.  In the past i've tried numerous ways to get started in real estate. I've tried doing wholesale and rehab deals, but sadly failed because I didn't do my due diligence correctly and gave up after not being able to find any hard money lenders and not knowing the next proper steps. I also tried to get my IL real estate license to sell real estate full time, but I failed the state exam 2 times and gave up. I was so frustrated. The only thing I've ever wanted to do with my life was to become a full time real estate investor and agent, but I failed - and with the pressures of friends and family around me telling me to give up, I did just that.

However after my accident, I've come to a realization that I should NEVER give up on my dreams. I need to go all in on myself and make no excuses. So what I failed? Time to get back up again and make it happen! -- here's my vision

I'm currently in the Chicago area.. But I have absolutely no interest of being here. I don't like much of anything about the state and I can't stand the long freezing winters anymore. I hear lots of people around me talking about how they hate it here, they hate the weather, they can't stand the taxes, etc. but they aren't leaving anytime soon thats for sure. I for one am completely different. I don't like my environment, so IM OUT! My goal is to leave within a year - to a year and a half and head to SUNNY Orlando, FL area. There's a reason I picked this location as my go to. I decided I wanted to become a full time short term rental host on AIRBNB somewhere close to Disney World. Also, I want to FINALLY pass the real estate exam - only this time I want it to be in Florida. Now to get to my question... 

How much money would you suggest I should have saved before I make the move?? Should I look for a home, apartment, or condo for the AIRBNB property? 

Also to get more specific... any Kissimmee, Orlando, Celebration or surrounding area agents out there willing to help me along this process of finding a property that allows short term rentals? 

Thank you so much for your help.. Your answer means the world to me