From my vantage, how would you go about starting?

[Dan Mead]

I'd like to get started in the vacation rental world and have decided to just put this up to see where you gurus take me.   I'm looking for the same old advice on how you would pull the trigger to get it done, from where I am standing.  I've poured through the site for quite some time, but still a bit lost.  I know this is the newbie in my just needing to get started!

So, here are my details.  

I have a full-time career, making a solid wage. Currently we also have a new mortgage. We had this house built for us, we love it and the location. Our kids like it too. For the moment, we are planning on being here at least a year, as then the HOA will allow us to rent it if we want. Regardless, we've made the decision to stay in this home for the moment, so I need to find another way to get into the market.

We have just over 10k set aside for investing, and we are actively saving more.  

As of buying this home, we have credit scores of 795 and 805.

SO! not sure what else would be relevant and don't want to bore you with details.  

I have my eyes on a few homes, which I would intend on fixing up a bit and then renting as Vacation rentals.  

Two of them are currently asking $105,000.  They are in an area where comparable rents are asking 140-300 a night.  I believe I would be able to get at least 50% occupancy, but would think i could get more.  I'm not sure how to go about testing that.

A conventional mortgage is obviously not an option on my own, as I need more for a down payment.   

So, how do I evaluate these deals better?  

There are opportunities everywhere, but what would you do to help get into the market quicker, to get started?