I thought it was incredibly hypocritical when I worked for a bank and got those requests from "risk management".

He doesn’t own another property at the moment free and clear to use as collateral.

I mean if you go to buy a car and offer the dealer the advertised price , then someone else walks in at that moment, and says I want to buy the same car , the dealership doesn’t make you bid highest price! 

My area I feel has very little appreciation at the moment although rental prices have increased rapidly over the past couple years (many landlords have not yet raised prices to what market can support). 

We cannot as we are out of country at the moment.

It's an incredibly thriving market.

We fought for this for several reasons: 1. tourism is our main economy 2. there are an incredible amount of dilapidated homes that could be renovated and made beautiful if the investment return justified it (which STR in a beach town could) and 3.this is a family-friendly, lower-cost and now COVID friendly way to travel. 

Development is one of those plays that either goes incredibly well or incredibly poorly.

May not affect your situation at the moment but something to keep in mind as you grow your portfolio. 

I've never had any issues or concerns about security but I know what I'm doing.As to the timing, like with most investments, yesterday is generally the best moment and today the second best.