House-hacking with a multi-family property is a fantastic way to get started—it’s one of the best strategies for learning the ropes of property management while generating income right from the start.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

The reference VP sounds fantastic though!

We were there looking for another property that we could buy together on the beach that we could rent out as a short-term vacation rental.We we're living it up and having a fantastic time zip lining, eating delicious food, and seeing the monkeys in the wild.it seems like from the moment I returned from that trip in August 2022 the real estate market completely changed.

.✅ 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.

It's super easy to use and will save you a ton of time :)The team at Steadily is absolutely fantastic!

Knoxville isn't a luxury market. widen the gap and do new construction. find infill plots of land in better locations and have more control. work closely with a builder who Is working with investors. we have flippers who did hundreds of flips then they graduate to new builds and say it's much easier. if you have the balance sheet you'll be fine. budget 20%. new construction commands a 20% premium and is much easier to duplicate Over and over and much less risk. 

Hi Diana - It's fantastic to hear your STR is thriving!

It also depends upon the CCRs themselves — they can control as to priority — and the date of the assessments in question versus the date of the lien being foreclosed.Way too many variables for an accurate answer across multiple jurisdictions.

I understand the two main downsides of condos being monthly fees out of your control and little appreciation.