thanks everyoneI am looking at zoned vacation rental condo's - like condolelsThere are many near the hotels that are long standing vacation rentals - zoned as such.I'm not looking at any residential airbnb type properties where special permits may be needed.This is strictly investment  - no stays or visits by me or friends.they are often called condotel's here as there is a front desk and check in - cleaning services somethings if you want.High taxes are a given - the main downside I see besides running them;) is if tourism slows dramatically - in this case they can legally be rented long term for a bit less.  

However the major downside is HOAs.

Cons : The down side to this scenario 1) you'll live next to your tenant (this can be a pro as well though because they can't hide from you and will be more likely to pay on time when you live right next to them), 2) multi can be harder to sell when you want to exit the property later on.

There isn't enough potential upside (I would want more than 12% IRR for a speculative appreciation play) to take on the potential downside, but that's just me.  

She also highlights the downside of short term rentals (having to be more hands on management, supplying personal items, etc).

I did some search on what that means and this link provided good information.https://generalliabilityinsure...However, I am still a bit unsure about if there are any major downside of going with an"excess and surplus lines carrier" vs a standard carrier.  

If I want $100k for a house, and I get 2 offers, one for $100k and another for $95k, unless I think I can significantly expand my upside for minimal downside risk, it would be foolish to reject and say "best and highest".

Dealing with family in this capacity really only has a downside for you. 

Even if the property pencils out strongly today the potential downside (economic slow down, recession, etc.) is to great for me to stomach.

What about the downsides?