Is there a rickety old deck that could collapse under the weight of 4-5 housemates and their friends?

On chairs, you’ll need to look at weight limits, because I’ve seen a lot with a low 225 lb limit.  

I'd weight the options of high EMD with an inspection contingency so my money isn't at risk, and low(er) EMD with no contingency and I could lose my money.

The shower curtain can also accumulate a lot of body grease!

The limitation depends mainly on the price and weight of the vehicle.

I forgot to mention, I suggest you confirm with the responsible government body (town, city or county) that the encroachment and proposed easement do not and would not violate zoning restrictions, i.e. setbacks or utility easements.

I'm a bit hesitant because sports have destroyed my body haha.

The purpose of the group is to connect with like-minded individuals who can help move each other forward faster.The same goal we start at "moving",  every body is stuck in the analysis-paralysis and they never start. 

And truth is it's far FAR more weighted on a person, the personality, vs any company organization or lack there of. 

A lot of times, these types of lifestyle choices will start limiting you down very quickly to specific areas, and since you are going to be living in the property, are likely to have a heavy weight on the neighborhoods.