And if so, what stipulations or worries should I consider before following through with this?

The major stipulation is that the HOA cannot be under litigation.

What kind of financing stipulates that I must live in the house for at least a year?

@Caleb Heimsoth Lawn care and snow removal are part of what he's supposed to do as stipulated in the PMA.

There's also stipulations with arms length transactions that you would likely be crossing. 

They might also be able to write the tenants a letter, and/or negotiate some kind of settlement or stipulation that prevents the tenant from taking legal action.

Also, if not bidding as an investor, homepath stipulates you must hold the house for at least 1 year before selling.

If it is going to take you 45 days to evict them, you add that amount of additional rent on file, with the stipulation in their lease that when they are "however many days late you choose", you get to file for eviction, even though they have additional funds on deposit.  

At any rate, we're going to require him to sign a new lease that stipulates month-to-month. 

Unless stipulated otherwise in the lease you will need a 28 day notice, which terminates the lease at the end of the following month.Here is a link to a Wisconsin Landlord Tenant Guide by the Department of Consumer Protection.In terms of legal notices, leases and other forms you need I would recommend Wisconsin Legal Blank, you can either order online or download the forms.Good luck!