So, if the parties negotiate with each other, it is always an element of negotiations to say to the other party something along the lines of, "You might be right in what you are claiming that you owe me only $XX, but you will have to hire a lawyer to find out, so save the legal fees and pay me $XX plus $YY, and it will still be cheaper than paying the lawyers." 

If both parties agree on terms (price, etc), you could always hire a RE attorney to go over with and explain the contract to the seller before he or she signs for probably a 1/2-1 hour consultation.

In 1988 I quit my job, started a consulting company, hired people, etc., etc. 

In this case I would be hiring people to do the work on the house instead of myself as it can get done quicker and I won’t get burnt on working on it every day after work.

Other option is to hire a lawyer to lobby for you, but that will be an expense, and the path of least resistance is to gain favor with the neighbor and council person.

There are ways to reduce the burden of short-term rentals such as hiring cleaning, a management team, etc.

I did hire him to renovate my NYC coop, and found that at the end of the experiment, although I was very happy with the quality of the work, communication between us was difficult and his subs were less than forthright. 

Or you can hire someone to write the letters and send them out for you. 

The guy I hired I asked to do a laundry list of tasks which included painting the exterior.

I could be way off on my assumptions which is why I hired an engineer to come by.