All Forum Posts by: Craig Sparling
Craig Sparling has started 9 posts and replied 19 times.
Post: Chicago vs the world: Forgone opportunities?

- Investor
- Chicago
- Posts 20
- Votes 11
One small word in defense of retrospection. One of my favorite authors, Nicholas Nassim Taleb, sold me on the concept of Skin in the Game and holding all pundits accountable for prior predictions, myself included. Only by reviewing past buy/walk decisions and market decisions will I be able to hone my chops for future decisions.
Post: Chicago vs the world: Forgone opportunities?

- Investor
- Chicago
- Posts 20
- Votes 11
Quote from @Dan H.:
For me it is not the markets i did not invest in as much as the properties i did not purchase. I lost one once that projected great return because i requested an estoppel before accepting the offer. Another offer came in and was accepted. I have lost properties for a few $k that were projecting return hat would have done outstanding even if my offer was noticeably higher.
back then, it was not whether you would make a lot of money as mych as if there was a different purchase that would produce a better return. I should have bought all of them 😀. I sort of believed that RE would always have plenty of opportunities.
Good luck
Post: Chicago vs the world: Forgone opportunities?

- Investor
- Chicago
- Posts 20
- Votes 11
Good points all. @Max Ferguson In the end it is all about what is next.
@John Clark I think the viable path to a presence element is huge. Reliance on a team a flight away wasn't for me as I was getting started, I am considering bending that approach. Indiana wasn't on my radar, but it seems like I could likely get some better fundamentals and escape Chicago's fiscal vortex.
@Aaron Zimmerman my old Chicago buy box (Albany Park, Rogers Park, Irving Park, Lincoln Square, Ravenswood Manor) has moved pretty far away from my preferred fundamentals. But I may need to dig a bit deeper or expand my parameters.
Post: Chicago vs the world: Forgone opportunities?

- Investor
- Chicago
- Posts 20
- Votes 11
I've been investing in Chicago for almost 15 years. I've been incredibly lucky with tenants, turnover, properties, appreciation, connections etc.
That said I do occasionally find myself wondering, what if....
If I had bought in Florida or Texas or a booming college town. Would slow and steady be replaced with meteoric?
Am I suffering from greener grass syndrome, or should I have "Lived where I want to live and invested where the money made sense."? What do you think the best "markets that got away" are?
Post: Crazy Chicago real estate Journey

- Investor
- Chicago
- Posts 20
- Votes 11
I've had two sewer backups in the last couple of years. One during a torrential rain storm and last week. We do preventive rodding, but I guess it didn't get the job done.
The city really screwed a lot of people with it's zoning and drainage. Insurance was a no go since it was backed up.
Post: Adding my portfolio: The OG, the cornerstone, my first child.

- Investor
- Chicago
- Posts 20
- Votes 11
Investment Info:
Small multi-family (2-4 units) buy & hold investment.
Purchase price: $350,000
Cash invested: $40,000
The OG, my pride and joy. I went big early.
Post: Fix to live-in, house-hack deferred.

- Investor
- Chicago
- Posts 20
- Votes 11
Investment Info:
Single-family residence fix & flip investment in Riverwoods.
Purchase price: $365,000
Cash invested: $550,000
Bought to live in, forced some equity and was able to get out almost all of my cash. 2.3% interest rate!
Post: Finally going on the grid

- Investor
- Chicago
- Posts 20
- Votes 11
I've been freeloading BiggerPockets from afar for years. Now I am officially in their database. I hope they are an even better experience beyond the credential wall.
Post: Flip and hold

- Investor
- Chicago
- Posts 20
- Votes 11
Investment Info:
Single-family residence buy & hold investment.
Purchase price: $365,000
Cash invested: $550,000
Bought and renoed a 1965 house into a modern farm house.