I didn't know I was inheriting this property and had never even visited it before. 

My goals haven’t changed, however, thanks to all the lucrative travel assignments and lockdowns I’m lightyears ahead financially. 

"pain and suffering", "future loss of enjoyment", "rehabilitation for the injuries" - 20 visits to the chiropractor who would need x-rays, MRI's to make sure there is no soft tissue damage, who the heck knows?!?

Thank you for the response.I decided on going ahead and cash out refinance my primary residence and property 1.While the cashflow will go down, I really should be playing the long game and continue to scale (like I wanted to do).Another purchase/rent increases should/will cover the losses in cashflow, while increasing amortization's.Really appreciate someone taking the time to reply and read, since I have no one else to talk to about these subjects.Thanks again!

Typically if a resident gives us a heads up that they will be late and are good residents we will work with them to an extent but try to get the rent paid by the 15th.

You may be ahead of your reserves for a year or two, but quickly can fall behind those your reserves, as budgeted.I take a very conservative approach, but not only budget all recurring items, like landscaping and snow removal, but also take the replacement cost of every item divided by the useful life (both physically and aesthetically) and budget that as well.  

I wanted to get some insight on how much a Contractor should charge for a site visit to a property.Thanks

The only exception to this is if people have cash to pay months ahead up front (which has some implications you need to be aware of and can be annoying should a hearing happen) or if their rent is paid by the government and they aren't responsible for any of it.

I would probably visit the cabin a few times a year and use it personally so that's where I think things would be a little tricky.

You could talk to them about making a deal where you pay them one month early so that if there is a problem they know well ahead of time.