Flipping is not a great option right now if you aren't experienced because regular home buyers are buying a lot of the dumps and overpaying, spinning the market for trash homes up too high to make any money flipping.

They recently cleaned house of a lot of the corrupt people and for now the wait times are worse than before.I had one project in a historic district- remember that the historic district department has a different intake deadline than the regular permit department.  

DTI had become my hurdle, making regular plain vanilla mortgages difficult.

As far as saturation goes when the boom was hitting we started seeing regular homes and even mobile homes get converted to “cabin/chalet” rentals.  

One reason they should be able to do that is literally because they manage a lot of properties and can toss contractors business on a regular basis.

Kudos to your regular buyer agent for "stepping aside" and staying out of a transaction where he/she might not be needed. 

If it is a regular rental, draw up paperwork that clearly outlines how much money they lent you, when it will be paid back and how much (eg if you buy a house for $400K and 10 years later they move out and it sells for $500K-do they get a percentage of the profit (after taxes and costs)?

I'd focus on getting a better property manager, their job is to shield you from most of these headaches and to prevent them in the first place through tenant selection and doing regular property inspections.

NY times did an expose on insurance company losses that should make you worry. https://www.nytimes.com/interactive/2024/05/13/climate/home-...

Notice may be given by: (A) regular mail; (B) certified mail, return receipt requested; (C) personal delivery to any resident; (D) personal delivery at the property to any occupant over 16 years old; (E) electronic mail delivery to the email address used by the Tenant to submit the lease application.