I have not had any experience with Easy Street Capital, but David Lichten resides in Gardiner, Maine and I have done many deals with him. https://kennebecrealtycapital.com/It's great to have options and compare, plus he is local! 

However, the best way to get a feel for rental rates compared to values is to review/underwrite properties in the area - only after reviewing/underwriting many will you begin to see a pattern.

There is a distinct difference in the law between short term and long term rentals. 

Through this journey, I’ve built strong relationships and developed valuable expertise in:Researching micromarkets and identifying comparables, potencial Accurately estimating construction or remodeling costs.Securing fast and reliable financing through partnerships with two top hard money lenders in Texas, offering competitive rates.I’m on this platform to connect with capital partners who are seeking an annual ROI of 12%-15%.

It’s worth calculating the total investment (purchase price + wiring replacement) and comparing it to what the property could yield after the upgrade.

You can find comparable sales in 2017 and use that dollar/acre figure to arrive at the fair market value then. 

 @Jordan Laney Asking what others pay for snow removal and comparing your yearly spend to past years is not productive.

Westchester, although one of the hottest markets, has a ton of upside with opportunities for both cash-flow and equity. 2-4 family properties in Westchester are the 2nd most affordable in the NYC Metropolitan area (next to Suffolk County) making it easier to find cashflow opportunities when compared to the boroughs and other suburbs like Nassau.A client of ours in Westchester recently purchased a < $800K 2-family with a detached 3-car garage which brings in additional rental income - from a local business owner with commercial vehicles.

In my experience it's easier to liquidate single family homes compared to other asset classes, that's why I like them better.

There are a lot of good meetups for real estate investors in the area that would be good to grow your network and learn from others that are and have been in your shoes as a new investor, message me and I can share on some specific monthly meetups.Also sharing some multifamily data, this is Boston proper so it has an interesting trend compared to the rest of Massachusetts.