As always, some bad actors cause burdensome regulations for everyone else.Per the Akron Cleveland Association of Realtors:"For example, in Cleveland, a local agent in charge must be identified if the property is not owner-occupied.

I don’t believe any jurisdiction is getting more lax on STR regulation.

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

Federal Laws Prohibit Discrimination of 7 Protected Classes, Massachusetts has added 8 more:-02.Always know more of the Rules/Laws/Regulations than ANY Tenant.

I give these threats no thought because 1) my actions are appropriate 2) i document well 3) they have yet to follow through with any of these lawsuits 4) typically their ignorance is apparent in what they are threatening to sue for. 

But keep in mind if your using money you cant afford to get back then buying action property might not be appropriate for your current endeavors and its better to just buy open market were you can do proper due diligence and know you have a build-able site.

I believe Hawaii will continue regulating STR and it will be harder to make the numbers work. 

If pool in ground is not an option or not in your budget, a quality above ground one could be a good route to go.I would definitely make sure you have an appropriate coverage.

Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed. 

This is a highly regulated activity by the CFPB.