You are going to send your wife to personally unclog that toilet.

.✅ 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.

@Nathan Johnson "Our savings are minimal, since teaching isn't very lucrative and life is expensive."

.- Navigating tricky landlord-tenant relationships when you live on the same property.While some people thrive in this environment, others find it difficult to balance personal space with their role as a landlord.### 3.

.- Loss of historical data (for both IRS audits and for personal portfolio tracking.)- Unfamiliarity of software with my Bookkeeping and Accounting team.

You will need to save that initial income to buy your first properties, get your mortgages, etc.You don't need a college degree to swing a hammer, but that psychology class could come in handy negotiating with a difficult tenant.

Literally to save their lives.

Definitely a personal preference.

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.

Some of the heavy hitters here in Chicago discussed the ADU program with a very nice person from the building department.