He is correct that a single ADU in a single family zoned area is unlikely to return as much as the hands off cost and is one of many reasons that adding a single ADU in most single family areas is not a good re investment.  

What would you do in my shoes I don’t invest there so take this with a slight grain of salt but I’ve heard multiple stories of basically this exact scenario someone getting offered a big payday for something in Cumberland, rejecting it & always for some reason (house burned down, block got worse, sheetz decided they actually didn’t want someone’s land for a car wash after all) always selling for like 10-20k and regretting not selling. 

Our main issue is these properties are owned in an LLC.

While the image of yours I found seem to show the main entry to the 2nd floor at ground level, the older the prospective tenant, the less interested they are in a non-ground floor unit. 2) Using another part of the property as storage could limit interest and I could see that as a turn off with folks once they find this out.FYI, the listing I found on realtor.com makes no mention of the tenant not having access the entire property or the basement being used as storage.

You're not in the position to be a cash buyer...as a former wealth manager, it's simply not a good play for you for many of the reasons stated above and more.  

Hi Joshua, the amount of down payment also changes with the cost of the property, so starting with a less expensive property may be smart (for multiple reasons).

@Scott E.Several reasons.1.

Throughout the year I come across situations where people need to sell there home due to a variety or reasons, job loss, income loss, health, divorce, etc.

For some stupid reason, I told our insurance about the incident. 

Quote from @Andrew Steffens: I think going into an STR purchase with reasonable expectations of cashflow in this current market and rate environment is admirable.