The problem I see my clients get into with vacation rental purchases when the intent is to get something they can enjoy as well is that many times they get tired of going to that one spot. 

This attracts people wanting to book "gatherings" and will have up to 10 people sleep wherever they find a spot, if we don't intervene. 

I’ve been doing a ton of research on it as I’ve been looking at Italy myself so I have been focused on the less densely populated but still very popular travel spots like Tuscany outside of Florence and Sicily though I’m nervous about Sicily and their major drought issues.

If you know New Hampshire well and what the hot spots and activities are there’s many areas with year round demand.

It doesn't take long to learn how to spot a good deal.6.

Before I buy my first property, I’m curious to talk with a financial advisor to ensure I’m in a good spot and figure out the most tax efficient way to pull together a down payment.

It doesn't take long to learn how to spot a good deal.6.

But I'd just spot-treat with Orange Oil and sister up the beam with lag screws...

I think only 20 spots is way too small to be worthwhile.

You are spot on and this is the kind of detailed analysis we are looking into now!