It seems like I'm never ready to actually turn my sales switch on because I can be awkward and it's something to work on but I feel like it gets easier after every phone call.

It also, seems like it may be a little awkward since I'll be living there too.

But some homes may not function as well as a 4 bedroom if it’s not fluid, it’s an awkward location, sqft of the house doesn’t support it, etc., and if your target audience or buyers in your neighborhood are middle/upper class, own their own business and need an office, etc., they may desire that more and comps will reflect that.Most MLS listings categorize offices/dens/bonus rooms all together and is often overlooked or missed on Zillow, Redfin, etc.

I ran a successful software development company for 27 years and had a incredible staff of very intelligent but social awkward engineers.

@Evan AlexakosFoundation/structural issues, awkward layouts, major sewer line problems, inheriting non-paying tenants, termites or other serious bug infestations.

In the future, to reduce exposure, I would probably rent through a LLC - either a large place in an awkward spot (i.e. on a busy street, not surrounded by homes) or a commercial office that was previously a home and turn it back into a residence.Hope this answer helps.Best,Dave

@Cheryl J McGrath there are many calculators, spreadsheets, and resources out there for analyzing properties, but there's no fool-proof app that can tell an investor everything they need to know about a property--because REI involves a LOT more than just data.For instance, a musty smell in the basement caused by water intrusion, a neighbor with a loud barking dog, a floorplan that's awkward but that could easily be re-arranged, significant settling, the location of load-bearing walls, the routing of electric, HVAC ducts, and plumbing  --these are just a few of the MANY factors that might cause me to buy (or not buy) a property, but none of these factors will be conveyed in data or on an app. 

They usually have awkward floor plans (and sketchy renos) and so much wasted rental potential. 

Only 2 awkward over the fence chats about home values with the nice people who bought it from me.

The bathroom is a nice size already so extending the bathroom out into that awkwardly placed bedroom would be overkill in my opinion.