For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

The best coverage is generally called "Special Form".  

If the lease sets forth how to clean these units with a special cleaner it seems charging the renter for the damage would be a possible move.

In the event you miss calculated your equity potential, you should be fully ready and able to settle the transaction or be prepared to lose your initial deposit. 

@Jake Berlin- thanks ...I would recommend getting a loan approval  started  using a hypotehtical purchase price and loan amt ...This will allow you to get  organized/ educated and  prepared  and many of your questions will be  answered - good luck

We understand this can be challenging for our tenants, but we are planning for our children's future and teaching them about the REAL ESTATE benefits.Do any of you have suggestions as to how we can best approach this or can refer me to someone who can prepare a letter addressing our plans for the build?  

Here's how to get started and advice on each area:Section 8 Rentals:Education: Learn about the Section 8 program, including eligibility requirements and benefits for landlords.Networking: Connect with local landlords who have experience with Section 8 rentals for practical advice and insights.Property Selection: Look for properties in Raleigh, NC, and surrounding areas that meet Section 8 housing standards and have potential for rental income.BRRR Method (Buy, Rehab, Rent, Refinance):Research: Study the BRRR method to understand how to find undervalued properties, finance renovations, and refinance to pull out equity.Partnerships: Consider partnering with contractors, lenders, and real estate agents experienced in BRRR to streamline the process.Market Analysis: Analyze local market conditions to identify neighborhoods with potential for property value appreciation and rental demand.Airbnb Properties:Regulations: Familiarize yourself with local regulations and zoning laws governing short-term rentals in Raleigh, NC.Property Preparation: Prepare properties to meet Airbnb standards, including furnishing, amenities, and guest experience.Marketing: Develop a marketing strategy to attract Airbnb guests, leveraging platforms like Airbnb and optimizing property listings.Overall Strategy:Continuous Learning: Stay updated with industry trends, attend local real estate meetups, and consider joining real estate investor groups.Financial Management: Manage your LLC, Opal Capital Holdings, effectively to track expenses, income, and tax obligations.Long-Term Goals: Keep your multifamily apartment goal in mind, and progressively scale your real estate portfolio based on experience and market opportunities.If you would like some help getting started, or just want to discuss please feel free to reach out to me directly.

I’m sure they exist somewhere, but the vast majority of small businesses just don’t generate the income nor the margins to hire the quality of people nor the specialized skills needed to produce without the involvement of the owner willing to wear many different hats, pick up the slack where needed, and work the hours necessary to make the business a success. 

I am an Army Public Health Nurse and fitness instructor/trainer preparing to retire after 30 years of service. 

Would really appreciate any insight you have on resources I should look into to learn more, point me to companies that specialize in this, or anything you think I would need to know to get started.