Your calculations should include utililies and repairs, legals, snow removal, etc.

Has anyone had any luck obtaining legal counsel and fighting this?  

They can and will fine you heavily and order you to remove it completely if you don't go to them first and ask for an inspection and do what they want to make it legal and permitted.Don't try to "get away with it".Be a businessman and fix the problem the right way.

If this is a big-ticket item, you might consider legal action against Airbnb.  

While it might feel counterintuitive, it can sometimes save you the time and cost of a legal eviction.I’d love to hear from others in the forum..Have you found any creative or cost-effective ways to navigate eviction challenges?

Holding properties in an LLC (or other legal entity) can offer valuable protection for your personal assets, so I understand why you went that route.

At the same time, someone else reduces your debt, and you get to use the tax code to improve your tax situation legally.  

If you buy it too low, in some jurisdictions they will call it "equity skimming" which is illegal.It can be very profitable, I've done many, but you really need to know what you are doing. on pre foreclosures on the West coast if you happen to do them legally .. the old owner is due 80% of the profit if you sell within 36 months.. so there is that.. but if your buying pre foreclosure for long term hold and wait out the 36 months then your fine. the reality these days is post GFC lenders/ banks/ servicers have realize that working with the buyer to reinstate recast redo the loans is far better than taking it all the way to foreclosure so your correct its usually the worse houses that make it all the way to the end and go to sale.thats why if you follow NODs  Notice of defaults or whatever they are call in your state. you see so many postponements and or removed or paid off etc.. so you hone in on one property do all this work only to have it not go  to sale  rarely are you going to buy a home that you really want LOL

Legal entities are set up for this purpose.  

Yes it's definitely legal, and I've sold a few this way.