He is not turned off by the 1980's decor inside and he is willing to let me update it as he occupies the building as I think most renters would be.

When I've been in this position in the past, I've marketed the home as a lease-purchase with an attractive Decorator Allowance (say $3-5K) that the resident will only get once they are qualified and ready to purchase the house, sometime down the road.Great tenants do want an attractive home, but they are often willing to overlook cosmetic concerns if they are given both the opportunity to purchase and the promise of a big check to make things pretty once they buy!

I'm also pretty skilled at all areas of design (I have my BFA in fashion design, part of the draw of my current home for Air BNB is how it's decorated, and I worked as a graphic designer to pay part of my way through college).

Buying a single family home means you're covering all these costs as well.Don't forget about the additional upfront costs especially since they're new builds, furnishings, decor, electronics, cable/internet, small appliances, kitchen wares, window treatments, etc.    

Hey @Chris Modzeleski Instead of boarding up the windows, install the decorative window bars to prevent the crazies from breaking into your property.

This tenant is unique though as she’s a great housekeeper very friendly and has it decorated nice which makes it appear better than it actually is lol I think it really just depends .

He sees my décor in the living room and says "Fook yeah we'll take this house". 

REPAIRS AND ALTERATIONS: RESIDENT shall make a WRITTEN REQUEST to OWNER/Agent regarding any repairs, decorations or alterations contemplated.

@Adam CraigSlate blue with white accents will made the gable decoration stand out properly, The biggest obstacle to really adding some period-appropriate fanciful decoration are the severe Tuscan columns.

Also, make sure you build in enough for janitor/maintenance/repair/cleaning/decorating/supplies/management (even if it's you now)/Misc.