The other benefit to verify is if you have loss protection.

The warm months are now approaching but, for the future, I'd suggest coming in aggressively low during winter months and looking for an 18 month lease to start - that way you'll renew in a better pricing period and see some income while you wait rather than spending three months with none.

You should only have to change when your current software has a flaw or lacking feature that is causing you to spend too much work on a work-around.

The laws protect vs detract the operations.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

There are a lot of inconsistent contractors, so really spend some time vetting them. 

We are t protected at renewal time. 

There are many reasons why I haven't pursued the arbitrage model, but mainly that it takes too long for the ROI after investing all your time and effort into buying furniture and renting and paying utilities.Let's say you rent an apartment for $1500 and you spend $7000 to furnished it.

There really isn't a safe, secure way for someone to protect their interests.

If I was in your shoes I would find ways to streamline your day job so that you are not spending as much time in that role.