ADRs are also compressing it seems from the data.Which cities are best to deal with when it comes to STR rules and regulations?

I've thought about it a bit, but the tax burden whenever I've looked here in The Netherlands has been pretty high comparatively speaking, and regulations are a bit tough to swallow as a potential landlord (even if I largely agree in principle with them). 

One - from the Investment company act for the overall fund structure. 3(c)(5) is an exemption from the investment company act for real estate funds.Two - from the securities act for the investments within that fund structure. 506(b) and 506(c) are exemptions under the securities act, which allow different methods for marketing the funds/syndications.More detailed breakdown:🔹 3(c)(5) — The Real Estate Fund ExemptionThis is part of Regulation D under the Investment Company Act of 1940.

Some areas define it as anything under 30 days; others under 90.Midterm rentals often bypass short-term rental restrictions — but you still need:-Proper lease agreements-Local registration (in some cases)-Business insuranceIf you’re operating in gray areas, tighten up your paperwork.Anyone’s city recently updated their MTR regulations?

Obviously this created a panic in my wife who is our PM, so I started running several of our most recently placed tenants and identified numerous inconsistencies in the reports Buildium was providing.

I wish I knew a perfect answer on how to regulate this. 

To me, that says that -- no evidence to the contrary -- he rented out in violation of the town ordinance and (my take) now wants to whine that he got caught.AirBnB and other short term rentals (STR) need to be regulated because they impose externalities on neighbors and deprive local governments of revenue and -- depending on circumstances -- pose unfair competition on local hostelries.

The numerous pop-up windows load slowly, and ACH fees for outgoing payments are $1 each, which adds up quickly.It's particularly frustrating that I have to manually create and apply a bill for maintenance fees to each property every month.

You should have some good economic reason for converting it.There is no court case or regulations specifically prohibiting this, nor telling taxpayers they can do this, from my experience, but again, you asking this question and it feeling a little "too good to be true" is usually a sign the IRS may scrutinize something like this, especially if done repeatedly. 

Every coastal town has a different set of rules and regulations regarding short-term rentals, so be sure to understand what the regulations are before you buy a place or you may end up being stuck with a property you can't use the way that you intend.