The data @Devin Conley posted is pretty solid from my experience (I do not know Devin nor how he sourced the data, just going by my own investing experience).  

2-4 unit in New England sounds like a solid next step!

We’ve worked together for about 2 years now, and he is focused on the operations side of the business.There are many solid sponsors and operators in this asset class, some newer than us, and some older – and quite a bit of new money coming into this space (part of this is where we are in the market cycle, and other asset classes being overpriced like apartment buildings).I’ve personally had several conversations with @Jefferson Lilly (and met him at a conference), and he knows the space well.

Not many people are excited to see long-time solid neighbors leave and have them replaced by a short-term rental. 

I furnished 2 STRs for that amount, just go to either high-end thrift stores or a lower-end antique store....you'd be surprised at how little you can pay for solid wood furniture...

Start here...have a solid lease with an Addendum of dealbreakers/rules that are written in plain everyday language. 

These are top drive-to destinations for much of the Southeast, so short-term rentals here can generate solid cash flow, especially during peak seasons.The area is also seeing steady growth, with more infrastructure and amenities being added to support visitors and new residents.

In 4 or 5 years you will have appreciation and a solid number of years with 2% remaining.  

When the time came to sell, I anticipated a solid profit from the deal.

If you're able to save $50-100K per year for 14 years (when you're 40), a combination of getting solid deals, paying down debt, and having a target goal of income vs expenses, it's definitely doable.