Software automates what you already know (hopefully) - for some folks they get in trouble because they assume the software "knows" and they don't bother to learn it.

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

Plus, if the property is in a desirable location, you may have little trouble finding tenants.However, there are potential cons to be mindful of.

Advice to install cameras may get you in legal trouble.

Once renewal period comes up (if they've been paying on time and causing no trouble) you can decide if you want to keep them or move on. 

Maybe through mediation you can get some more money out of the seller for your troubles.  

I recently talked to someone locally to me (Ohio) who got in trouble with the LCB for giving away a bottle of wine with his luxury rental as even that was considered selling it. 

Question for the RentRedi users: do any of your tenants have trouble with the fact that everything is done through a mobile app?

They are highly motivated to produce profit, and our interests are fully aligned.

This has caused me to have trouble with getting approved for loans/mortgages due to my work gap.