Has anyone had experience working with them before or this kind of model? 

Purchased a buildable infill lot for $10,000 in an HOA, with similar lots going for $30,000+.

We plan to hold this asset for 3-5 years.

With that said, my goal with advance booking is to bring-in a decent amount of revenue during the offseason (winter), but don't want to scare anyone away with a large initial deposit, and of course I'd like to discourage cancellations.  

Any preferred vendors for this and recommendations on the best way to set this up? 

So someone who is looking purely to maximize potential return (and has unlimited time) is unlikely to find this a good fit.You can also hire a property manager for direct real estate and have someone oversee them, making direct ownership more passive.

Time Requirement.You must spend more than 750 hours in real estate activities during the tax year.And you must spend more than half of your personal service hours in real estate activities.3.

Unfortunately, you are stuck with the monthly mortgage insurance.

As I've learned more about analyzing properties I have quickly discovered we had to make some changes to our current rents and with changes going into effect next month the property will cash flow around $675/month, we only have about 7 more years on a small lean we have on the building, after that it should cash flow around $1000/month and be paid off with no leans. 

Although I’ve been a long-time member, I’m just starting to engage more actively here.