We use Quickbooks Online for our main accounting software.  

Short-term rentals mainly cater to vacationers.

Mainly how or if you offer them at your STR.

There are many folks, including myself, in this forum that can help and the more info you can provide (mainly numbers on the property), the more we can help you.

The property would be in a C+ to B- type location, with cash flow as the main objective and appreciation second (75/25 split).

It's my understanding that the city is responsible for all the piping up to the curb stop in my front yard and I am responsible for the curb stop to my property.Yes from the water meter to the house is generally the owner and from the main line to the meter is generally the city.. 

They used to be marketed with all of the other homes on the main search page, but a user had to go into the filters and specifically select the "FSBO & Other" tab.

My main focus is Class B and maybe some C+ properties around NE Columbus, as well as outside 270 from the North to the east side.

One main regulation I find in Ontario Residencial Tenancy Act section 134 (3) states you cannot make a profit in subletting.

The main issue is land... or lack-there-of.