If get somebody inexperienced at a discount, you are taking a chance. 

If you’re not already using similar software, I’d highly recommend exploring these options—they can save you a lot of headaches down the road.

However, with Software to make it easier to manage properties efficiently has helped tremendously.

A good investor agent that is plugged in with local wholesalers, is prospecting, and marketing on their own will have plenty of discounted off market opportunities that will have less eyeballs on them then the MLS.

What we have learned is that most people avoid these properties entirely, which allows us to purchase them at a significant discount.

Let's say my competitors are at $100/night.. what's a reasonable discount?  

Hopefully, based on actual field measurements, past project data, and estimating software, your contractor can develop a detailed estimate that lays out the cost of labor and all materials for each phase of the project.

As an experiment I invested $30k each in the 10 REITs which had (according to average estimate of NAV) the largest discounts from net asset value as per market price).

Depending on the development of the software, it would be interesting to see if AI can replicate the role of a listing agent.

Quote from @Basit Siddiqi: I personally would not buy real estate with a retirement account.There are just too many headaches that are not worth the potential increased return.Some headaches when it comes to investing in real estate with a retirement account1) LTV values are less and harder to find lenders.2) Potential to sell or partially distibute the property if you have to do a RMD(Required Minimum Distribution)3) If you run out of cash and have to make a major repair, you may be out of luck and have to sell.4) Having to potentially worry about UBTI(Unrelated Business Taxable Income)I would personally invest in stocks/bonds/notes with a retirement account.I buy deals with cash and use a ROTH SDIRA so there are no RMD's.I buy at huge discounts to retail.