I don't do app development but I was told for most sites and businesses it's a lot of work for low payback.

Just tap into what talents you do have and offer that in exchange for shadowing and learning about the business. 

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

This is a fine needle to thread because at this size, you very quickly start competing with high net worth individuals who are seeking summer homes. 

Here are my two cents...I recommend starting in a market with strong fundamentals, such as steady population growth, an influx of major corporations or large businesses relocating to the area, an affordable cost of living, and high rental demand.

Most importantly, they are disrespectful and bad business people.

Dig and remove around 200 square feet of an old concrete driveway, frame and lay down the concrete (concrete will be ordered from concrete supply business) and complete a brick ribbon around the driveway.

You have a far better chance trying to sell to an individual than targeting hedge funds.

Hey everyone,I'm looking to get started in the short-term rental business and could really use some advice.

If you have a business you can grow and get financially rewarded that is higher priority then leaving that.