Focus on key areas first (like floors, walls, kitchen, or bathroom), which may help you handle the costs more gradually, even if it means moving in furniture or updating fixtures down the line.Also, since the tenant left it in rough shape, be sure to document all the damage (photos, receipts) in case you decide to pursue reimbursement through their security deposit or in court.

Usually, a single-member LLC to avoid filing separate tax returns.

Talk with some securities attorneys, brokers, lenders. 

As far as your primary residence, if you have lived in it 2 out of the last 5 years, you should not have to pay taxes on capital gains (difference between what you paid for it & what you sold it for) up to $250,000 if you file your taxes as an individual and $500,000 if you file jointly with a spouse.Just a disclaimer, I am not a tax professional.

End to end, I bought the land, secured permits, got the PPA and IA, SUP, and still own the project.

Safeguard reached out to me when I was in my mid 60s, and offered lending notes secured by real estate. 

I liked the tenant, school is starting back etc, I told them they could pay first month and security deposit and I would let them have the rest of August for free.

I have filed for eviction on one tenant that I have placed in my career, and I was able to negotiate him out long before the court date. 99% of the time, eviction should not be a driver for whether you invest. 

As I’m nearing retirement, I just invested a similar amount in first trust deeds secured by real estate at 9.75%.

If you’re not well-versed in lease agreements, security deposit rules, or eviction procedures, you could run into trouble.❌ Emotional Stress – Handling tenant issues (especially late payments or evictions) can be stressful, especially if you live in the same building.Hiring a Property Manager in ChicagoPros of Hiring a Property Manager✅ Less Stress & Time Commitment – A property manager handles everything from finding tenants to collecting rent and coordinating repairs.