I most want to avoid spending considerable time showing units in-person to prospective renters, esp. before we've pre-screened them.

And it's only been worse each year after.Today, the auction is a great way to overpay for something.

Love that you are coming to the market to interface here, nothing can substitute it in my mind.  

I am on an H1B visa and new to rental properties.

We also started repeat visiting Chincoteague, VA annually, and so decided to give another STR run here.

You also want to make sure you have Replacement Value so that if anything catastrophic happens you can rebuild.

The best way to do this is develop a great working relationship with a real estate agent or escrow officer and they will provide you with reports for free. 

One upside to me would consistent rent scale, meaning if you upgrade one unit early, you set the table for all of the units when done because they are all the same.

Quote from @Rachel Marshall: Talk to your lender.

I got into the industry primarily to learn about real estate investments specifically long term rentals/ the BRRRR method so when it comes time for me to do my own deals I have the confidence and knowledge to do so.