Hey man,I feel your pain, everyone has gone through it.This is what you should know...As you keep doing it, you will start to get better at it.

Haha I'm starting off small so it's not so painful if I make a mistake ;)

The laws vary by jurisdiction and are a pain to keep up with.

We try to add so much value that it strongly outways the painful taxes. 

I don't hear of it often, but I have heard directly from city inspectors that they've made people open stuff up, get permits and get it inspected, so that can be a real pain and expense.   

Home Warranty (far from perfect, many people don't like them for a lot of reasons mainly because they are a pain to deal with, but as a safety net for someone looking to get going despite not having super deep pockets yet, they are worth looking into IMO, just pick a company with a good track record, and often you can have your agent pay for it as a closing gift). 

Or just block it off when they book 3 days if they want the extra day.

The licenses are limited per block based on number of existing rentals.

With that said, I think it is important to highlight the pain points of Short Term Rentals that often get glossed over by new and experienced investors, or those looking to get into the industry.

We're trying to acquire the whole block : ) How did you find this deal and how did you negotiate it?