I will have people that expect to rent my nicely renovated 4/3 3000sf with private pool, fenced yard on a lake for $100/night because they saw some other dump a couple blocks down for that price.

I'd love to utilize their expertise when assessing a property since they are local but I'm not sure what the general expectation is when I don't have a tangible property and I have not entered into contract to work with them yet.Some questions I have are: local regulations/permitting timeline, property's potential from their perspective, landscaping/amenities cost estimate (they also help facilitate this).

If you renovate for a flip and then decide to BRRRR you will likely get less than you expect because the finishes will be too nice for a rental (depending on the neighborhood, it could work where you are in that price point).

I don't know how many deals like this I could do on my own before I could reasonably expect my worst-case results to be a loss of $16K.

With 4 more properties and 24 more rooms we expect to onboard in the next few months. 

Ants, spiders, flys, and other ordinary pests are often brought in by tenant behavior, so it's reasonable to expect them to handle with removal.Bed bugs are 100% the tenant's fault because they do not travel from home to home on their own; they have to be brought in.

I would start by setting expectations that you will likely not be able to net as much as you would if the property were vacant and turnkey. 

How much time and money should I expect the eviction to cost?  

Quote from @Kevin James: Do you own AT&T?

My question is what guarantees should I expect before paying?