Sorry for the confusion, I am buying and holding SFH homes and putting a section 8 tenant in there.

My point is, you are on the right track with your thinking, so now to the "HOW" to actually get in, if like me, you don't have an in or connection.First step is likely to get licensed, if you aren't already there are some other ways to get in the door and be helpful but licensed means they can pay you cuts of the deal and its less upfront cost and risk to them in helping you out.  

Know that every long term lender will require a survey and if something comes up on it when you are trying to sell or refi, you could get stuck in hard money without an easy or quick way to get out.Is there a pre-payment penalty?

Be mindful that there are rules that the lenders want you to check off.Furthermore, there are other rules on the tax side where you want to normally be under to get the most tax benefits.The magic number in both instances is '14 days'Lenders want you to stay atleast 14 days to meet the secondary home requirement.The tax accountant normally wants you to stay less than 14 days or 10% of the days it was used as a rental to treat it as a rental and not as a personal residence.Best of luck!

Brian,Because VT is a traditional rental market (ski houses), depending on the minimum duration you will be allowing for rentals (ie. monthly, Weekly, etc.) there are some regular carriers in the New England Market that will write it. 

The team is already there - they do everything.

I took on an occupied property where the tenants had been there for over 10 years, and no inspection had ever been done.

Be sure to explore all around the forums as well as many of the FREE tools that Bigger Pockets provides.I am on the lending side of things and am always happy to hop on a call to discuss loan options that are out there, even if not offered by my resources.

If your goal is to attract high quality tenants with consistent rent increases there are city/towns that have more favorable laws that I would advise you look in instead. 

I've only been in a week so far, I'm hoping there is a little more structure for new members than there seems to be at this point.