This would be quite the analytical marvel to even effectively ESTIMATE this with any reasonable level of certainty/confidence (even for someone appropriately trained). 

From May – Oct it appeared the inventory leveled out but in November we are currently seeing a 200 unit increase over October.

I develop a high level scope of work and then make my own estimates for each item.

I also think that if there is any downturn, entry level vacation rentals in places like Kihei will feel it much less than high end luxury vacation rentals and hotels. 

At a high level, this is generally the path people take - we see a lot of people have success in this route - start building the portfolio with banks, low down payments, and then **generally** when you hit around 5 or so properties - it starts to make sense to switch over to LLCs, its too hard to qualify/deal with paperwork of banks and switch towards private lenders like DSCR Loans - (LLC friendly, easier) to scale past 5 or so.

At first this sounds like a good thing because its a cheaper entry level but the more you own the more complicated life can get.

At my level of properties, I don’t think the price per month justifies joining Buildium

Excited about learning from those doing it at a much higher level than me, and networking and educational opportunities seem excellent as well!

As a general rule of thumb if the property has a ground level commercial requirement in order to show sufficient hardship to seek a residential use change the property should be located in a location that is not conducive to commercial use i.e residential street, close but not as marketable as properties located on neighborhood's primary commercial corridor etc. 

The only way you can break that log jam right now is severely lowered fed rates, but the level of federal debt is such that they're in a no-win situation because there's going to be little appetite these days for buying 1% fed notes from overseas.The fed rates were kept too low for too long.