To win the STR game, especially if you're a new entrant, the most important aspects are 1) Amenities2) Location3) Property type4) UniquenessAll are geared toward you standing out on Airbnb/VRBOHot tubs, fire pit, bowling alley, pools etc. or being in the best location in an area as well as being to host a large group are all things to help you win.

They are usually funded by very wealthy people or a group of investors pooling money together.

Regarding your lender pool, are you going to residential lenders that happen to dip their toes in the water of DSCR?

When it comes to analyzing properties, I’ve developed a specific checklist to make sure the home fits both resident needs and operational goals:Square Footage: Ideally, at least 2,000 sq. ft. to ensure enough living space for residents and staff.No Stairs or Pools: It reduces liability and keeps the home accessible for everyone (this is just my preference).Corner Lots: I love corner lots because they often provide extra parking and outdoor space—both of which are critical for families and visitors.

In June 2024, we completed installation of a heated and chilled pool.

The "online leads" trend becomes a vast pool of scams, each one discovering a new and "better" way to find motivated sellers via SEO/Paid adds/Social Media etc, and automatically aims to make a profit from selling those so-called leads.

Can anyone provide insight on the average cost of insurance for Airbnbs with pools in the Boston area?

Now I have seen a situation where there was a pre-2016 build, but the previous owner pulled permit to install a pool and a new Certificate of Occupancy was issued after 2016. 

It’s worth researching to see if this might be a good fit for your situation.Lease Structure and Clauses: Work with an attorney to draft a lease with strong clauses for late fees, maintenance responsibilities, and other terms to protect your interests.Target Stable Tenant Profiles: While no tenant is risk-free, targeting tenant pools that historically have more stability (e.g., retirees, dual-income households, or tenants relocating for work) may reduce risk.Stay Up to Date on Landlord-Tenant Laws: Understanding your rights and obligations can help you navigate issues more effectively if they arise.That said, if the potential risks are keeping you up at night and the financial pressure of an eviction would be too much, selling may still be the best option for peace of mind.

Then clear a pool below a spring and rock formation.