This borders on government over reaching and is no short of a straight up shakedown. 

Any potential government intervention to remove the stress test or increase the amortization period for CMHC insured mortgages would most likely increase demand.

Philly is at the lower end there, at 1.4% of value, but you also do have higher transfer taxes there, more rental regulations, and more tenant-friendly laws & courts.

I can easily google for 50-200 acre plots of undeveloped land all over the U.S. for under $100k, but I'm thinking there's another level of scale I'm not seeing, such as government grants, auctions, etc.

Investing overseas seems a bit daunting, but like you mentioned,  it could be easier to find a great deal due to less competition -  you just know about the different rules and regulations of that geography.

Cleaning fees are a pass through and so are the sales and room taxes so unless you intend to "eat" the cost of them (which you shouldn't have to), the fees will be paid for by the guest and you just pass them through to the cleaner and government (in the case of taxes).

But I need to research the local government/city side for rules governing STRs.

These screening services need to access government records to find out if anyone has been evicted.I wonder if Tellus actually has people who call to verify income and employment.

LOLGreg title co and title insurers are heavily regulated.. you think they are going to risk their licenses to get a 50 dollar kick back.. 

Downside is your dealing with the government and you can't refinance until you've lived there 1 year to pull your equity out.Hard money loan is not owner occupied and you can't live there while you are in the HML loan.