.✅ 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.

However, on my back burner is a direct booking site and I'm leaning toward OwnerRez (once I get through Ski Season).

As such, you qualified for a truly self-directed Solo 401k plan (as long as you don't have any employees working for you).

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

Some used more creative ways to handle the needs but it is still a capital call and dilutes the return (if anything left). 

I’ve noticed that STRs with those kinds of unique offerings tend to stand out and get booked faster.Looking forward to seeing what direction you decide to take!

I come across SFR in other states from time to time direct to seller. 

Each team would propose a new ideas and new creative financing to help both sides reach their goal.

That sounds like someone who has been going in the wrong direction financially for whatever reason.

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