This meant I couldn’t pursue the driver personally and had to rely on their car insurance, which settled for $25K—their maximum coverage.Unfortunately, the crash added $77K in unexpected costs, including $41K in repairs and extended holding costs.

Plus say another 4 feet with the person standing. 

If you know what you do and why you're doing it, there's no need for the bad and the ugly, which I personally haven't experienced.

When I go to get more work done, I use the person that was fairly priced and met my expectations that first time, I do not shop around again for the lowest deal.

Quote from @Nate Meeker: Great insight, I am personally choosing not to file these for clients, but am providing a free guide to help them.  

Need some advice on the best way to structure this deal that's fair and beneficial for a 3 person LLC/partnership agreement. 

It's been a very, very bumpy road to be under contract - and past the due dilligence period - on a new build we are purchasing with the intent to use it as a STR (and some personal use).

Here in Chicago, we've found some of our best contractors from other good contractors or investors; I've found the in-person meetups yield the best results, so maybe you can take a trip to Maryland? 

Despite having photos available, many prospective tenants still prefer to see the unit in person to get a better sense of where they'll be staying. 

I personally feel that it is a liability people could use as an excuse for an accident they have if they are drunk.