What are some of the challenges an owner would have accepting this type of deal.  

You are touching them and providing some type of education and value to them to bolster your own status, so when you ask for money they are more likely to say yes.And, back to investors or deal first, no broker will ever award you a deal without a reasonable surety that you have the capital lined up.

Yours looks like it is a bit more work but I would definitely do some research before spending that type of $So far the consensus is that this is steep but these guys quote these prices to insurance companies, but unfortunately we are paying out of pocket and cannot or i should say I do not want to pay these prices. 

What made you interested in investing in this type of deal?

Ski Leases: Looking at the short term rental policies it does not cover leases longer than 30 days, seeing as there is a market for this type of rental what are peoples experience with this for ~4 month terms, and has it worked for summer leases as well.?

I think those are the type of jobs Waco needs in order to really take off.

What type of trouble am I in?

Best is subjective.I'd recommend speaking to a few PMs to see who aligns with the type of management and fees you're looking for in a property management company.

However, I feel like they probably wouldn't have banned him had he attempted to provide some type of honest explanation for all of the inconsistencies.

The click on / locking type seems like what most investors use, but repairs seem difficult without having to re-do a large area.