Unique pieces are great for "Flair" and individuating your property but if it fits in a suitcase and isn't fixed to the wall or floor then it will not be long for your STR.

They don't allow auto payments or automatically add late fees, and tenants would have the option to pull their payment back, which is not ideal.

I am conflicted on whether to use the 500K on one big property (ideally multi-unit) or buy several smaller properties.

Of course your individual experience may vary and maybe you have a marketing and sales background so it is a good fit.

This is ideal if you have a full-time job or don’t want to deal with day-to-day landlord tasks.✅ 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!

For example, if your driveway only fits two cars, you need to know if tenants plan to bring several vehicles, as this could lead to parking violations and HOA fines.Don’t forget to screen pets, too!

@Diana Teng there are a LOT of potential pitfalls:(So, it's vitaly important to not just find someone that you think you can trust because they tell you what you want to hear, but you find someone that their processes seem a good fit for what you want.EXAMPLE: we do BRRR Turnkeys for clients and take numerous vides we share with them - initial, worst state of any demo, when HVAC, plumbing, electrical update BEFORE walled in, before any major payouts and of course a final walk-thru video.One thing that's accurate from all the HGTV renovation/flip shows is that you should expect and plan for surprises!

Ideally, this would be just one step in a larger plan to grow into multiple rental units over time.

@Lauren Ruppert Yes, an LLC can sell a property to your child’s LLC, ideally at fair market value (FMV) to avoid gift tax complications.

Commercial programs a heavily dependent on location and NOI (less one size fits all compared to residential).