We have purchased a piece of land and intend on running a seasonal STR on the property.

Love that houseI have definitely considered doing STR on the units that have entrances off the alley, but both have long term tenants (10+ years) in place that I’d rather not displace. 

I'm a little confused as to how this was worded- if you're planning on being owner occupied on the one side and having the STR on the other, or if you're thinking of having a long term tenant on one side with a STR on the other. 

Looking into purchasing a STR on Maui in Kihei. 

Live in one do STR on the others.You get great cash flow and get to build equity at the same time.

Second: we are purchasing a STR in ScottsdaleThird: we are purchasing a condo in Nashville that is STR only.

We are selling our home and relocating to a new house that has a nice apartment built in the attached garage.  We are considering doing a STR but curious about challenges of having guest while raising three children. ...

Because there was one other STR on the block ahead of me, these people knew that a STR means immaculate properties inside and out, and an owner that cares.Let these neighbors of yours know that because of you, this property will always be the nicest in the area.

To a person they were all relieved...because of another STR on the block having been kept immaculate and they were already seeing how nice I was making it compared to how it had been for years.

I would stay away from HOAs if you have intentions of possibly turning it into an STR on weekends.Also, you should check with your insurance company to see if they cover short-term rentals.