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

Private money and personal funds.

i think this is a decision only you can make. im in a similar boat (house hacking my primary) and considering renting the whole thing out to get a solo home for myself. certainly a lot of appeal in that, given how much work goes into the house hack. but whether or not the numbers on cash flow align is up to you. personally i dont think $150 (seems like about 12%?)

@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.

This is a very personal question that is difficult to answer. 

As far as whether to approach them with or without an agent - approaching them directly without an agent can save the seller probably 2.5-3% of fees, which give you some room to negotiate on the price, but you need to be confident that you are capable of evaluating the property value, estimating on the amount of work that is needed, knowing how to negotiate/ structure the deal, and navigating the closing process.

It's stronger in court if they do it, nothing personal.

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

There is an amount that you can distribute from an IRA account to purchase a personal residence.You then might be able to turn the personal residence into an investment property.Best of luck.

.✅ 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.