I am specifically looking in Essex county, MA because I want to house back close enough to my current W-2 job.

However, I'm unsure of the specific areas within these states to target.

Houston STR definetly has a more specific need.

There is no specific amount of days either that the guidelines call for that you occupy the property.

Both my wife and my background is in manufacturing, specifically operations, customer service, and project/account management. 

But guess what, rates WILL drop in the next few months/years and most markets will explode after that IMO.If I had 25K I would look into B or B+ (specifically with schools above 5 greatschools rating, and moderate to low crime rate confirmed by heat map and frequenting businesses there) areas within 25 minutes driving distance from my home for a SFH. 

Hey @Ashley Kroft I love using Pricelabs feature of creating a comp set because you can really drill down to the finer details of what others are doing in the market, in your specific area.

For example, do you have any specific skills around social media?

Our buy box specifically focuses on vacation destination accommodations - including boutique motel/hotel, campgrounds, treehouses, cabins, etc.   

@Michelle Hardy Just adding, check your local city too for their requirements, many have specific requirements that the state may not have.Here in VT in the towns my properties are in, there is not a requirement to keep them separate or pay interest.