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

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.

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. 

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

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

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.

Yes, this will be an entry level job, but it gives you experience, gives you income to be able to even start buying single family rentals, if you want, gives you connections in the industry (not always investors, but people you may need later on).  

For sure, don't just believe what a few luddites on BP have to say.One of the few in here who understands the space from a macro level. 

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

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.