So the initial appraisal for the refinance was good at the time, but now the As-Is is not gaining traction with buyers.

By working for a larger corporation you are gaining an unfair advantage, by letting them train and develop you (while you are getting paid) and you do real estate on the side.This idea is not from me, read RichDad. 

Many of them use RE crowdfunding platforms to gain more exposure.  

But this will also lead to future inflation.The issue is going to be the rich will get richer as they can live with lower cash flow but gain appreciation.

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

Do you guys see the benefit outperform the 2~3k price difference? 

It's a forced equity and appreciation play with the benefit of personal use and the hope that 100% bonus depreciation comes back.

I really wanted to pursue this not so much for the financial benefit but for the learning experience.

Hey, if you get married you'll be able to shield an extra $250k in capital gains!!

This location is in a 1mm population metro area, 230 units, and cost is about $1,800,000 all in.Limits of Insurance: Coverage:Liability and Medical Expenses$2,000,000/$4,000,000 Occurrence/Aggregate Comprehensive Business Liability$2,000,000 Any One Person Personal & Advertising Injury$4,000,000 Aggregate Products Completed Operations Aggregate$2,000,000 Any One Fire Fire Damage$25,000 Occurrence Customers' Goods Legal Liability Deductible: $0$25,000 Aggregate Sale and Disposal Liability Deductible: $1,000$10,000 Any One Person Medical Payments $1,000,000 Occurrence Hired Non-Owned$300,000 Each Employee Employee Benefits Liability$25,000/$25,000 Per Claim/Aggregate Employment Practices LiabilityLoc Class Desc Coverage Limit Ded Valuation Type 1 Self-StorageBlanket Building & Business Personal Replacement Cost Property $2,100,000 $25,000Earthquake IncludedSinkhole IncludedWindstorm or Hail Included 5%Business Income Actual Loss Sustained 24 MonthsPollution Clean-Up & Removal $100,000Employee Dishonesty $15,000Money & Securities - Inside $10,000Money & Securities - Outside $5,000Accounts Receivable $25,000Electronic Data $20,000Valuable Papers & Records $25,000Fine Arts $10,000Employee Personal Property $10,000Limited Pollutant Removal $25,000/$100,000Cosmetic Loss Limitation IncludedEquipment Breakdown Protection IncludedPremium, Fees, and Taxes: BOP Premium: $ 7,760.00Optional Terrorism Premium: $ 31.00Total Premium: $ 7,791.00Key notes:a.