It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

@Greg P.Given your objectives, if you extrapolate your numbers it would take 97 rentals earning $300/month to return $350,000 per year.One thing to keep in mind is that not wanting to invest locally and self manage, you will also have significant property management expenses.  

Writing them down turns your ideas into tangible objectives you can work toward.

In any case, you can easily calculate that.Looking at your objective of retiring in Costa Rica, you have two options:1.

I would keep the carpet neutral but something easily washable cleanable.As others have said, I'd add other decorative objects like artwork.

Does anyone know, or have a good idea, about the difference in returns on entitling & developing the land for each scenario, with final objective to sell to a builder to build and sell the structures him/herself.  

A friend of my wife put it it best: "The last time I trusted someone, I had twins."

The bank valuation should obviously be a useful objective view on the valuation of the property.

I mean, how shady is it to object to that?

My view it’s that it’s always better building a brand rather then focussing purely on the aggregators (whether Airbnb or otherwise) but it would depend on your objectives as an investor/operator of your own spaces.