We both work W2 jobs and don’t use the income from these investments.

I on the other hand am begging for him to try a cpa since there’s alot of new concepts with maintence vs improvements etc for tax purposes.

Major issues like foundation work, bathroom renovations, and deck repairs are considered capital improvements, which can be depreciated over time, allowing you to offset a significant portion of your rental income with those deductions.

Identify necessary repairs and improvements.2.

I would like to get something setup to help connect all of the different teams you would need to do a full job from finance to maintenance and everything in between. 

There are new neighborhoods & jobs popping up rapidly in the area and expanding further South into Tate County, MS & Southeast into Marshall County, MS.

A good Accountant or Bookkeeper will work with you to tie out all your accounts and let you know any issues or advice as it comes up throughout the year.I would be more than happy to chat with you more about your finances, I was one of the few Bookkeepers to be invited to BiggerPocket's Financial Service offers and have been working with them on ways to improve it as I help more and more investors with their Books. 

Owning 25 doors, I interview all my tenants, just like a job interview.

In the next 1-2 yrs I'd like to move out to either a bigger place or a new new city (job related relocation etc).

Has he  been working remotely for his job in Canada?