Only 1 CRE property on the schedule of real estate all increase risk, so your lender would combat each risk point with offering lower leverage.

In particular, I've seen potential for this to happen in Grand County (Winter Park & Fraser) + Mount Crested Butte.

You'll want to make sure you understand the K1/tax filing implications because if you own very small piece of let's say 10 properties in 10 different states you would potentially receive 10 K1s (one for each deal) and 'may' have tax filing requirements in 10 states. 

For the kitchen and bathrooms, would I need to do EVP for potential water issues? 

This would help you potentially qualify for an FHA loan when you execute the purchase option.Option 2: 5% payment for the option with the option payment spread out over 12 months from the 2nd month until the 13thmonth.

I usually say something like, “we encourage future potential guests to read all other guest reviews of our property for an honest assessment of what to expect.”

What's the higher risk investment? 

The last thing you want is to inadvertently overlook or forget crucial details, potentially leading to complications down the road.

On the other hand, some disadvantages of HOAs include the potential for restrictive rules and regulations.

Look into different asset classes and see which fits your risk level and goals.