Purchased 1st property with existing tenants: general questions

[Robert Hughes]

Hey Ya'll,

I had a couple questions regarding buying a property with existing tenants. I close tomorrow on a 3 story Victorian using the VA home loan (1st home ever). I have 2 tenants that live in the 3rd story, 1 bedroom, apartment. They are on a month to month and have been in the property for just over a year. I've heard nothing but good things about these tenants. The second story apartment is now vacant because he was a nightmare. As a condition of closing he was to be evicted. So I still have a couple tenants and I have only met one of them because the other works 2 jobs. I haven't had the chance to have an in depth conversation with either of them to really learn more about them. Their current rent is 750 and market price for the neighborhood is 800-850. I'm also upgrading the second story apartment (4 bed, 1300 sq. ft.) and raising that rent from the previous amount of 800 to market price of 1200. My girlfriend is going to sell her house and we are going to move into the 3 bedroom apartment on the first floor and house hack. Now that you have a little bit of background to the property, on to the questions:

1) Should I make the current tenants go through the application process as new tenants in order for me to get more information on them or have a sit down conversation with them.

2) Should I require a year lease like I am going to with the second story apartment? 

3) Should I instantly raise rent the 50 dollars or keep them where they are at? Or add a progressive rent increase into the rental agreement.

4) They currently pay rent on the 15th. I'd prefer rent to be on the 1st to make concurrent with the future tenants due date on the second story. What is the best way to go about making this adjustment. 

5) Is there any legal reprimands to instilling new lease/rental rules and regulations (located in upstate NY) that differ from what is currently in place if the previous owner didn't have formal rental documents or lease agreements?

Those are just some questions off of the top of my head. Any further advice would be super appreciated. Thanks!

V/R

Robert