Instead, in advance (by days generally), I sign documents needing a notary at the local Wells Fargo, then overnight mail or have a broker pick up the executed documents.

I recently had a guest cancel on the day of arrival due to heavy rain in their area (not mine)!!!

Technically, if you put 50-75% down almost anything would cash flow but then you would be cash in heavy.

As a first-time landlord, I'd feel comfortable renting this out knowing that it will not need heavy repairs and know the area wellWhy renting will not make sense:1.

It covers everything from the specific start and end dates, quiet hours, common space sharing, overnight guests, etc. 

During very heavy rainfalls the whole thing gets emptied into Lake Ontario!

If you do not apply by today and you are going to use your home/cabin as an overnight rental, you will be required to bring it up to current building codes.

I only advise people to get into short-term rentals IF you are going to make it your ONE THING and go all in on that...having to set up all the necessary systems is a HEAVY lift and not worth it without scale...I have done it and not at scale and it was not worth the hassle. 

A 4 bedroom unit would be in the $100K range.This means I'm looking for older homes in the older parts of the city.The buildings may be more rundown and need some extra maintenance but it makes it easier for me to get cashflow out of them.Your approach should always be to find deals, offer 15-20% under asking price, be prepared to negotiate, and lean on your team of experts for the heavy lifting. 

Multiple, billion dollar companies are investing heavy in our area, such as Intel, Google, and Amazon.