Some people’s comfort zone is in having a rental that is renovated and in an area that may have high demand and consistently better looking neighborhoods.I have rentals in Taylorsville and Murray and enjoy those areas.

I'm very familiar and comfortable with CA markets but they are so high I know I'm missing out.

I don't expect we can bring someone in at a premium rent with the exterior looking like it does need the maintenance and I don't expect they'd be comfortable paying it based on a promise of a future upgrade.My plan B was to inform them of the upgrades up front and offer two options.  

If you were in their shoes, wouldn't you get "hooked" on that too? 

People track it indoors on their shoes, etc.

I understand this is personal comfort/risk appetite levels, but I'd like to hear how other smaller investors getting into the REI landlord arena think about this aspect. 

I could comfortably set up 3 park models with my own money and having it ready. 

Assuming you are looking to live in and rent (SF house hack) I would start by finding the areas you would like to/be comfortable living in then look into the pricing to buy and rough rents in those specific areas.

I remember being in your shoes and getting my first assignment check after finding a home that looked abandoned.

My goal is to continue to acquire rentals but ensure that they are cash flowing comfortably...