There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

One of the biggest challenges is keeping the bathroom as carefree as possible.

I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

Challenges?

Our property has HOA-mandated fences and faces a lake.  

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

As someone relatively young, obtaining a conventional loan has proven challenging for me.

Challenges?

Managing vacation rentals remotely sounds like a unique challenge..

Let's also face it, if someone doesn't have 500-5,000 in the bank as a wholesaler for EMD on their deals for their own business, another red flag.