The biggest challenge I'm facing is knowing what assumptions are reasonable. 

I'm trying to head into the process with my eyes wide open, and yet . . . it snowed here today, we're both working from home, and I've been distracted by internet real estate sites and pretty, pretty condo listings. 

If you use one of the more standard ADU plans then the biggest permit issue will be the DPP delay while they work through their backlog. 

Your biggest issue, @Alex Brewer, is that it's going to be very difficult to get any new development started at the moment.

If you were to look back on your investing career what have been the biggest mistakes you’ve made?

Yikes, well first off take a deep breath and be thankful they are out...they just solved your biggest potential problem.

@Ricky Solon That's the biggest lie in this industry and it makes me laugh every time I hear on the radio.

I would definitely be interested in hearing more about the financials, as that seems biggest hurdle for me right now. 

The biggest thing is to make sure you have some kind of income or savings to live off in the next few months. 

The biggest issue for dealing with OOS investing is the technology; make sure you research your boots-on-the-ground company to ensure they have paired with the right technology that will allow for easy communication and quick access to updates on your project, especially if you plan on not being on-site regularly.Make sure the "connections" you make with other GC's or REI professionals, that they are licensed and insured and can provide references for their work.Join local groups on other social media platforms and start discovering the midwest market virtually by hearing what others are saying/recommending and what areas people are investing in and with what REI strategy.Indianapolis is a great market to get into right now because you absolutely can stretch east/west coast dollars further.