This could be something that's completely case by case, but I was curious if there might be some official regulations or whatever.

The inspector may ask you to open up a few sample walls to check inside for proper work practices.  

In other words, firms get experience because all the do are oddball cases or they do enough vanilla cases that, statistically, the oddball cases come up.And, no offense, but the kid of a lawyer doesn't have the working knowledge of a law firm's business practices. 

Regulations forced banks to dump properties during the GR, which drove much of the huge price crash.

The pricing of these loans used to be 1-2% higher than a Fannie Mae loan, however the regulators for Fannie and Freddie put additional restrictions on Non-Owner occupied loans which caused the rates to increase, so there is close to no difference in the rates as of right now.

I'm not familiar with CT laws or real estate practices there, but in NC you can terminate the purchase during the "Due Diligence" period (you put down DD money to have the specified time...usually up to 3 weeks) for any reason or no reason.  

Or working with county regulations when there is inadequate access via a bridge.

I would simply be weary and really understand what rules and regulations exist before you make a purchase.

It seems to be a fairly common practice.

When I say I am new, I am very green in practice - outside of buying and selling my primary residences and renting out part of a property I own, I haven't don't much else with real estate.I have put quite some time into reading up on different topics in this area and watching podcast, webinars etc.