I guess if you have decided to gamble strictly on appreciation on a single fam, small multi, or other type of property, then you might 'overpay' if you think the property will appreciate in a time frame you find acceptable.

Second best would be a single sale as a portfolio...but the convenience of a single buyer likely comes with taking a slight discount, but it may not be too significant since for a buyer they have the advantage of a ready made portfolio. 

Either way, when starting out, the house hack is often the way to go because it has the potential to lower your entry and carrying costs (you have to live somewhere no matter what you do) and it lowers your risk because you are in a more convenient position to manage it than if you try to buy a rental 1,000 miles away with no good boots on the ground in that area.Best of luck!

There is no way to know if the next 20+ years are going to be anything like the last 20, or where etc. it is very risky to gamble solely on appreciation, but as long as you are never forced to sell it could be very worthwhile. 

I'd  like to have an opportunity to discuss the market with you when it's convenient. 

Is the gamble of little cash flow worth the potential opportunity in appreciation, tax benefits, loan pay down and potential refinance in later years?

People who want to wholesale with us want the convenience.

I also found the list of smart locks https://wisepick.org/best-smart-lock-for-airbnb-more-convenience-less-hassle/.

For example, “Excessive noise is any noise that is under human control and of such a nature as to unreasonably interfere with the peace, comfort and convenience of any person.”.Every city and county have their own noise ordinances.

People here have convinced themselves that the lower risk assets are gambling, and the higher risk assets are safer.