I'm looking to buy houses off market for personal investments.

You will likely need financing to scale (especially to scale quickly), and investment property mortgage will not be cheap or even available with poor credit. 

How did you handle tax prep when you first started investing, especially with a plan to scale over time?

If house hacking isn't the best option for me, how would you recommend starting out to build up some investments.

The IRS may challenge such transactions if they appear to be step transactions or lack a legitimate business purpose.Here are some things you might be interested in / want to consider:As @Andrew Kubik mentioned, since the property is now an investment property, you could consider a 1031 exchange to defer taxes.

For a true investment property, you'll be lucky to make a 10% IRR...so it would probably be better to invest that money in a 401k or 403b instead.

I have a property in Memphis...and frankly no matter how much I've spent on property management (have had three, all promise the sky and deliver next to nothing), I have gotten the run around by the property management team in all three cases, which has deterred me from investing further in Memphis real estate.

@Chase AlexanderRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

@Zack Whiting - You are in a top tier market for investment properties!

Here's the deal:Purchase Price (PP): $95kRenovation Budget (via HML): $60kTotal All-In Cost: $155kARV (After Repair Value): Around $200kRefinance (via DSCR Loan): 7% interest, 30-year fixedRefinance Details: After the refi, I will pay back the Hard Money Loan (HML) at 11.95% with 3 points:HML: $60,000Interest/fees: $3,585Other costs: $1,800Total to pay back HML: $65,385After the refi, I will have $84,615 left in cash.Cash Flow & Expenses:Expected Rent Income: $1,700/monthProperty Management (PM): $126/monthInsurance: $100/monthTaxes: $126/monthMortgage: $1,043.75/monthTotal Expenses: $1,395.75/monthSo my monthly cash flow is about:$1,700 - $1,395.75 = $304.25/month in cash flow.Return on Investment:Cash Invested After Refi: About $18,385 (after paying off HML and closing costs).Annual Cash Flow: $304.25 * 12 = $3,651Cash-on-Cash Return (CoC): $3,651 / $18,385 = 19.8%I didn’t account for maintenance costs since it’s a full gut rehab, and everything is brand new.