The contractor will be your biggest challenge.

Here are the biggest mistaken assumption unsophisticated investors make when contemplating an investment in a deal1- that the Sponsor is an expert in the field of investment2- that investments, economic markets, financial markets are predictable with any accuracy3- that PROJECTED returns are PROMISED / GUARANTEED returns4- that because they NEED their investment to be liquid the sponsor will provide said liquidity5- that the “deal” is more important than the sponsor. 

Quote from @Mike Johnson: Hi everyone, I was curious what might be some of the biggest problems to you run into while managing your properties?

Did you notice which of your updates made the biggest impact on your final sale price?

I would recommend increasing revenue density this way, etc etc." 

Stick to these tools, and you should be significantly happier with your next renters  Thank you, I did screen all aspects and everything looked good in the beginning but the biggest problems seems to be the renter big off more than they can chew.

Starting to consider whether to convert one of my LTRs to an STR. I'm already familiar with some of the basics of how the markets differ, but I'd be curious to hear what some of you have experienced in regard to any ...

One thought would be for you to move into the smaller unit and rent out the larger unit to bring in more revenue.

My biggest concern with ADU’s on single family lots is that all the new laws have muddled what the long term value looks like, and most people don’t realize it yet. 

The biggest hurdle I have with convincing ppl to househack is they feel like they 'deserve' to live alone, they've put in the time with roommates in college, etc and they wanna feel 'grown-up'.