Like Jake Baker suggested, keep good records and have a dedicated bank account for your property, properly separating personal and business expenses.

You might also want to look into supplemental insurance for future stays, like Proper Insurance or Safely, to cover situations where Airbnb’s support falls short.I'd be happy to help more.

You don't need a mortgage broker, just a reputable, competent direct lender that will ask the important questions upfront to properly screen your deal.

I invite you to perform the exercise and find what your cap ex allocation should be.certainly $50/month for maintenance/cap ex and misc is not enough and this property is definitely cash negative when properly allocating for expenses.  

The bottom line is this: Concealment is not asset protection, proper (time consuming and expensive, I know) management, and good, prudent, practices (ditto), WHICH ARE ADHERED TO, and insurance (expensive), are needed for asset protection.

Take ownership of your mistake and learn to do the proper due diligence recommended above😊

Generally speaking, Boston proper is an appreciation market (low cap rates) unless you have a solid value-add play.

Take ownership of your mistake and learn to do the proper due diligence recommended above😊

Consider consulting a CPA and attorney to address tax implications, liability, and ensure proper documentation for your multifamily investment partnership.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.