I am betting for the appreciation of the house in the next years because I don't think I can cash flow in the first years.  

If you don't want the property any more a 1031 is probably your best bet, unless it's got a huge capital gains capture in which case you could just take your tax lumps and collect your funds. 

Your goal is to reach as many potential buyers as possible, and right off the bat you're limiting your pool of buyers.

I've been researching the topic of limited liability and the different options to achieve this.

Here's the bet: - "Unemployment" is not about to shoot up.

Primarily self limiting beliefs.One of my clients just closed on their first commercial deal and they only had one duplex before I started working with them. 

In some very attractive markets like coastal cities I can see it being worth it not to rent the unit or rent it only under very limited circumstances in the low season because the high season is just too lucrative to allow anything to affect those bookings.

Rates are usually 10%+ and they’re limited 70%ish LTV.

There are limited number of companies and equipment. 

HCD would likely squash any jurisdiction’s attempt to remove or limit a safe unit.It is a good investment to get the unit permitted especially if it is close to the quoted price.