In 2018, the HOA issued a violation and informed us, we need to repaint the entire exterior of the house.  

Is there any practical reason to get these fixed now as opposed to waiting until I sell?

Also I have not formed an LLC, but not opposed to creating one either. 

(It'll be considered personal care as opposed to assisted living because of the size).I have two interested parties who would like to rent it out, but my dilemma at this point is actually figuring out just how much to charge for rent, in addition to what I'm responsible for making adjustments on as the owner. 

While interior upgrades are often a top priority for landlords, the exterior of your rental property is just as critical, if not more so, when it comes to attracting quality tenants.

The equity capture at the buy would essentially be your return as opposed to a CoC return.

This was the result of finding a property that was mismanaged and "looked" bad, but it really just needed surface level modifications to look good again (appliances, paint, some exterior work, etc.)These deals will pop up if you analyze properties consistently.

However, in the current layout, the two floors have their own front doors, and are only accessible to each other by exterior stairs, and both floors currently have full bathrooms.

It needs trees trimmed, a deck installed and exterior landscaping.

We built a new deck, refreshed exterior paint, and added flower beds to improve curb appeal.