There are still restrictions on setbacks from property lines, but local zoning and HOAs can no longer stop you based on the state law. 

Many of you probably know the „german“ way of doing things...The stereotype would be the punctuality and precision of the people and the public authorities.The reality is the following: a lot of barriers and long approval processes as well as legal restrictions when it comes to owning and handling capital.

There are about 10-12 other resort communities with similar amenities and have no restrictions on how you manage.

It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.I'd actually highly suggest Michigan because there is WAY LESS restrictions.

In Worcester, I think your numbers are pretty close, but there are also a lot of Programs between Mass Save, and the City of Worcester that will pay for many of these things if you agree to an income restriction, or sell income restricted. 

Of course, if your local ordinances restrict occupancy numbers, you can safely follow those ordinances. 

Do they violate any existing restrictions?

Some lenders will offer a blend of the two with something like a 14 year term.If a lender asks for more, they're imposing additional restrictions over and above what SBA requires.  

A lis pendens from the bank was filed 10 years ago, but the foreclosure was put on hold because of the SCRA restrictions protecting an active duty service member from being foreclosed on.

Your 3 options are 2 of the most restrictive in the country and own of the least.