Quote from @Patrick OHalleran: Hi David - I used HallCPA for a Consulting engagement (about $5k) and found the tax planning support to be very helpful. 

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

That is our plan with all but 1 property. 

@Olga DaiselI think we are lacking some key details of your plan.

Future enhancements include the planned Silver Line rail alignment with nearby stops, as well as potential commuter bus services, pedestrian paths, and bike lanes.The development benefits from proactive rezoning by the city, transitioning the land from industrial to mixed-use urban development.

Since you only have 2 full time and two part time staff, who covers their vacations and sick time?   

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

You Can Only Have 35 Non-Accredited InvestorsRule 506(b) allows an unlimited number of accredited investors but restricts you to only 35 non-accredited investors.However, there’s a catch:Non-accredited investors must be financially sophisticated.They must have enough experience to evaluate the investment risks.From the SEC:“Securities may not be sold to more than 35 non-accredited investors… [who] must meet the legal standard of having sufficient knowledge and experience in financial and business matters to be capable of evaluating the merits and risks of the prospective investment.”If you’re planning to include non-accredited investors, make sure they qualify—or you could be violating SEC rules.3.

I plan to use a HELOC but would be interested in the thoughts of others in BPs on this approach or recommendations if there are other ways to financing that I should consider.

What's the plan with the property?