If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

As long as no “healthcare” services are provided (like medication or personal care), it’s not regulated by the Department of Health.

What's your thoughts on using Rent Manager for an investor that already has professional property management?

But I am in FL, and Im sure that scares others, but I am not just talking about natural disasters - just general over-regulation. 

.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The other challenge is selling it, there is a smaller buyer pool for hospitality in a small market but that was known going in Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Licensed in both Hawaii and Vermont at the moment, navigating acquisitions and depositions by collaborating the directions of my client with grounded professional understanding. 

You should consult a tax professional for an answer based on your unique situation, this is not tax advise just general information.

Posts like this are part of my journey to learn, network & connect with experienced professionals like yourself who have valuable insights to share.I also want to apologize for the late response—it’s been a busy few days, but I didn’t want to miss the chance to thank you for your input.Looking forward to learning & growing in this space & who knows, maybe one day I’ll be offering you in on an investment idea or I'll be the one offering advice to new investors!