Prime (high demand Vacation Rental Property I want to sell them so I can retire, it is a complete Business with all components are in place, nothing needs changing just take over what I have created, I will provide full operational information, and be available for as long as needed.  

Find an attorney and an accountant you trust- see if their philosophies align and set things up the way that they advise.

It wasn’t until the last few months that I realized I would say that forever if I kept waiting for the stars to align.

We traded getting into the market (with reasonable rents) for higher cap expenses than I perhaps anticipated, haha.Besides looking at the age of major components of the house, is there a better way to estimate cap expenses? 

There probably is not one set number because it will depend on the age of a property, the age of the system components, if there are maintenance records available for the properties you will be looking at and other factors. 

If you do decide to invest out of state pick the market that is most aligned with your investment goals.

There are annual contribution limits to both a Traditional and Roth IRA.Furthermore, a traditional IRA can have both a deductible / non-deductible component(You would need to keep track of your basis in the non-deductible component).I personally do not like to invest directly in real estate through a retirement account.The issues you will potentially have are1) If you have to have excess funds within the retirement account for items such as improvements, tenant turnovers.

Of course, that's an emotional component, which I would just see as a 'math problem' now.Also, the homes were cheaply built and required capex to sell at year 10. 

@Nghi LeI disagree with @Ashish Acharya   The 15.3% self-emmployment income tax has two components:  12.4% for the FICA component, and, 2.9% for the Medicare component.  

I think there can be some good opportunities there, I just felt they ultimately didn’t align with my goals at this time.