$900K lakefront new build finished - Sell + start over in Midwest (Chicago?)

[John Yingling]

Hi there, I'm new here. Have been reading for years though. 

I'm single, and just turned 40.

I made a sizeable sum of money late 2021 / 2022, gasped, and bought 5 acres of lakefront land in upper Wisconsin, then GC'd my own 3BR walkout house, 2+ car garage, as well as a 1 bedroom / bath guest cabin. It went surprisingly well, considering what could have went wrong. Everything is paid for in full.

I put about $800k into it, all in. It was a heck of a learning experience.

Upon seeing the tail end of market FOMO, I tried to sell for $1.2M, and it didn't go. Lowered to $1.05M toward last fall, and still nothing. I strongly believe if we re-listed this for $950K, it'd go rather quickly. I've got them both up on AirBNB, and year 1 was about $6,000. Year 2 is already more than that in bookings. However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.

Bills / property taxes are about $12,000 a year.

The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.

I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.

I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,). This would be some serious wiggle room for not only moving back to Chicago, finding a job, but then start hitting the pavement on purchasing. I'd like to own a distressed 2 flat, and begin diving into the areas.

The goal would be a to take a 10 year plan of moderate - high risk, and turn $900K into retirement money by 50.

Any thoughts welcome.

Thanks.