I'm curious to hear everyone's biggest headaches or areas you wish you could change about owning, managing, buying, selling, or researching (etc.) real estate.What would make your life easier?

I have found a ton of new material on Craigslist if you are willing to hunt.The biggest issue I can see is that if the place looks rundown as you go on until it is finished, you risk the ratings on VRBO and AirBNB taking a hit.

The biggest issue, IMO, is safety.

Your biggest challenge will be finding a reliable cleaning company who STR experience.  

The biggest problems I see with wholesaler numbers around here: 1.)

The biggest mistake I see new wholesalers make is getting started before they know what the heck they are doing.

My biggest concern being the quality and making sure I don’t steer away potential buyers and sellers.

@Wes Eaves, Self storage is a strange combination of the biggest of the big and the smallest of the mom and pop. 

The biggest incentive for me to go the ADU route is that the space already lends itself to be an "easy" addition as its already semi-finished with egresses and ceiling heights that already meet code.

Purchase price: $450,000 Now performing as one of Colorado Springs biggest bedroom count AirBNB's.