I pay them $15 per reservation to give me $1500 of content coverages on each booking which covers most incidentals.

Is there a chance that rates and prices decrease in the next 1-4 years as our cash reserves increase, thus creating a better scenario for us first time investors?

I would have about $30k - $40k for a down payment, closing costs, and a few months of reserves. 

@J Scott please confirm.

We now control a $500,000 dollar asset AND still have cash reserves of $100,000. 

Run  some 220V wiring in pvc underground (licensed electrician) to power a good pump if you have space/amperage reserve in your electrical panel. 220V requires less current to run than a 120V for the same power, so it's more efficient.This guy has a lot of good videos on diy yard drainage systems.

If they don't show up, we just keep on keepin' on.As a private Landlord with no office, it's probably best to call them 30-60 minutes prior and confirm their intent to show.Another trick is to set showing times or have an open house.

So this wouldn’t kill my cash reserves for the next deal. 

Insurance companies are under extreme stress right now, although most still have strong reserves

We then have an umbrella policy for additional coverage and I add damage protection to all of my reservations for additional coverage.