I know there are some STR regulations, but it seems there are plenty of parts of town where it can be done.

Ironically its the investors in the layered LLC's who believe they are hidden in the cloaks of secrecy and better protected who end up in  the most costly and drawn out litigation while giving the plaintiff attorneys reason to take a more thorough look under the hood.Keep your LLC ownership simple, carry appropriate insurance, make sure ever vendor you work with carries appropriate insurance and those who perform work functions most likely to lead to liability exposure list you ad additional insured (not merely certificate holder) and it should go without saying, avoid negligent conduct.

This is just markets behaving normally, Austin was my first target two years ago once I got wind of the permitting and homebuilding we saw the long coming in and whether it was 2,3 or 4 years the entry point was way in front of us.I don't know if anyone gets "use to" 7% rates without home prices behaving and/or wages responding appropriately.

I am currently researching the different regulations in Ontario and GTA.

That is why I am moving to STR because I am tired of all these regulations popping up everyday.Sucks that you had to replace the toilet, and they rejected the payment.

- Legal and Regulatory Concerns: Are there any local laws or regulations in Fredericksburg, Virginia, that I should be aware of regarding pets in rental properties?

If you want to fill your property with residents sourced from the companies above, imagine being the overworked, relatively low-level employee tasked with finding the appropriate housing ASAP.

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).

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

Carry appropriate insurance (property, general liability and make sure you are listed as additional insured under tenant's renters policy and 3rd party vendors).