I would like to avoid all that ahead of time, though, by encouraging her to find acceptable housing before he moved into mine.

Just to set the record straight, the city can't require you to replace the 60 amp panel because it is "grand-fathered" - meaning if it was up to code when it was installed they can't force you to replace it now or in the future. 

Do your homework and plan ahead. 

Many of my rentals I will have rented for several years straight then down about 1 month for touch ups/repairs.  

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

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!

Im getting a traditional mortgage instead of hard money straight off the bat so I don't have the pressure of a high interest loan, I'll be using a primary residence mortgage and generally want a back up if I cant cashout refi for some reason. 

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.

Of course you can do it yourself and there are resources in the area to help you steer a straight path, I'm just recommending you consider the alternative.

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.