I use google drive and FreshBooks but it's a lot of in my head of who I hired and when they need to be done.

Readers should seek professional advice.

That said, I haven’t managed a long-term furnished rental, and I’m wondering if it might be less stressful.For context: I’ll likely need to hire a property manager since I’ll be overseas, and I want to make sure I’m not locking myself into a hassle.

I may hire an attorney, but I may have finally found a law pertaining to this issue.

Are you doing it yourself or hiring a contractor that specializes in it?

Readers should seek professional advice.

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

My overall goal for my professional career is to start an investment firm and own a big multifamily portfolio and get into development.

I use Stessa for accounting, I love it, it links right to my bank account/credit card accounts and I can assign purchases to different properties and units of the property for multi-unit properties and at the end of the year I have a simple report to give my tax professional 

Most of them do not and can even hurt you - as your S-corp with rentals. yeah this was under the guidance of the tax professional i went to.