@Jay Hinrichs @Jonathan Greene @Nicholas L.you have all helped me to really consider what type of challenge / path I want to get into, and all this information is excellent.

As others have stated, your fit & finish goals should be guided by whether you plan to:1) Rent: tenants don't always take care of a property, so you want to use lower-grade materials and workmanship.2) Flip: higher quality on workmanship and materials is usually required.Regardless, you always want to "Maintain to the Neighborhood".

3: Does the property fit with your current investing goals? 

We do take many steps to consider whether a tenant will be a good fit for the property.

You bring up an excellent point about the trade-offs between second home and investment property loans.

The interest rate is 2.375% so I am having a hard time letting go of the excellent rate.My question is: To scale from here, should I sell it and buy a fourplex as a house hack? 

Most home owners are only familiar with California Closets pricing and automatically perceive closet fit outs as being expensive.

Quote from @Marcus Bledsoe: This is an excellent thread @Jonathan Greene.

The worst tenant I ever rented to fit this concern exactly. 

Cardone fits that mold.