Quote from @Devin James: Quote from @Andrew Syrios: “If you want to increase your success rate, double your failure rate.”- Former IBM CEO Thomas Watson This is my first time hearing this..

However, planes of that era couldn’t stay aloft on one engine for long, doubling the risk of crashing into the Atlantic Ocean without any added benefit.

Let’s say I invested in another investment which doubled every 7 years.

He abandoned trying to scale.Learning from this experience when my partner and I decided we wanted to double our net income, we realized it would take a increase of 2 1/2 time our volume and probably need to triple our deal flow.  

@Gash Nookala,Renting can indeed be slower in winter, but here are some tips to boost interest:Enhance Listing: Ensure your listing has detailed descriptions and high-quality photos—consider professional photography if needed.Competitive Pricing: Double-check local comps; even a slight price adjustment or incentives (like a reduced deposit) could attract more interest.Broaden Marketing: Beyond Zillow, Hemlane, and MLS, use social media, community boards, and local business connections to reach a wider audience.Flexible Lease Terms: Offering shorter or month-to-month leases might appeal to tenants during this slower season.Local Property Manager: A local pro can tap into their network and help fill the vacancy faster.These steps should help you find a tenant despite the seasonal slowdown.

So we are doing a double flip with both the house and the land.  

She spent countless hours on the phone—with me, the city, contractors, and other key players—to help find the best path forward when she didn't have to.What I Learned:Insurance is your safety net: Always double-check that you have the correct policy for your project type. 

"pay me double of my expected assignment fee upfront., or in escrow and I will terminate it.

  $200/month divides into the $100K initial negative equals 500 months to recover the initial negative equity.Let's double the cash flow to $400/month.  250 months to recover the initial negative equity so over 20 years.Let's reduce the negative equity position to $50K (which likely is less realistic than expecting $400/month cash flow at that rent point), you are at over 10 years to recover the initial equity position.Now let's do it with all cash, no financing.The 50% rule state $900/month cash flow.  900 * 12/200K = $5.4% or about half of lifetime return of S&P 500, or what can almost be achieved with a zero work, zero risk CD.I see no way that someone who understands the numbers will call this a good investment.Note just because an investment is better than most other investments in a market does not imply something is a good investment. 

So my first question is always about what's the geographic scope.Anyhow, Milwaukee metro went up 8.2% in 2024, but when you break it down by community you quickly find that the highest % increases were municipalities with property values around 200k for a single family home, well into double digits.