Analysis Paralysis: Where do I start?

[Andrew Sullivan]

I've dove deep into the realms of real estate wisdom, heard every guru spiel, and read more how-to guides than I care to admit. Yet, here I am, stuck in the bog of analysis paralysis, feeling more confused than when I started. 

Flashback to my glory days at 16, slinging pizzas and dreaming of real estate riches. Fast forward to now, a fresh 24-year-old, recently booted from my cushy W-2 job paying $80k/year, left to ponder the meaning of life and the potential of my bank account.

Now, I find myself in the trenches of self-employment at my buddy's small business lending firm, with a 1099 in one hand and $75k in student loan debt in the other. Oh, the joys of adulthood! But as Frank Sinatra said ~That's Life ~. I'm determined to achieve financial freedom and live the life I always dreamed of.

Let's talk numbers, shall we? We've got expenses dancing around $2-3k per month, a modest $10k stash, and a student loan payment ($725/month) the size of a small country's GDP. I also have $58k invested in individual brokerage accounts and $22k in my Roth IRA. Although some may say this is impressive, I feel so far behind.

Now, onto the million-dollar question: How does one embark on a real estate journey with pockets as empty as my social calendar on a Saturday night? BRRRR? Single family? Section 8? Small multifamily? Large multifamily? Flipping? Sub-to? Wholesaling? Scott Jelinek Slow flip? Storage facility? Car wash? Laundromat? The possibilities are as vast as my confusion.

"But wait," I hear you say, "what about flipping? Cash is king, right?" Ah, if only it were that simple. Sure, I've scoured Zillow like it's my job (which, let's face it, it sort of is), but the only properties I find are nestled snugly in the heart of the Midwest, a land as foreign to me as quantum physics. I think this is where I would get the most value and it definitely has the most opportunity but again, as foreign as a flip phone. 

So, what's a broke, bewildered aspiring real estate mogul to do? Do I gamble my last dime on a single-family cash cow, or do I roll the dice on a flip and hope Lady Luck is on my side?

I'm at a crossroads, folks. I've had my fill of gurus peddling dreams for the price of a small island nation, and I refuse to sit idly by, twiddling my thumbs while life passes me by.

So, here I am, dear reader, baring my soul and begging for guidance. Will I emerge victorious from this real estate labyrinth, or will I be forever lost in the sea of "what ifs"?

Stay tuned for the next episode of "Real Estate Roulette: One Man's Quest for Financial Freedom," coming soon to a blog near you. And remember, laughter is the best medicine, especially when your bank account is running on fumes. Cheers to the journey ahead! 🍻

P.S. If you have any job openings I would love to send my resume over so let me know! :)