By the time they research and go down all the rabbit holes of different strategies, never sticking to one in order to gain traction, they get exhausted, throw their hands up and never take any real substantive action.Pick something and go with it, all the way to its conclusion.  

In 30 years the balloon payment is due to the seller and that's when the taxes are due.Coupling a monetization loan to an installment sale accomplishes the same thing but puts cash in the sellers hands that can be re-invested.

The property was handed down to my wife's siblings after her dad passed away.

Hey Mike I wanted to know if I wanted to seel you my home with seller financing and I  wanted to transfer title to you the buyer. unlike contract for deed WHAT is the instrument they use in Wisconsin.

I have seen this in Milwaukee too many times, the only way to make it work is VERY hands-on.If you end up renting it in March for IDK net $200 the property will have lost a LOT more in the next 12 months just in condition vs what it looks like now (assuming that it is freshly painted?

A lease is much like a deed, you have transferred legal rights to this property to the tenant and have taken on legal obligations for the maintenance on the property.

I've largely stayed away from the "sub-to" buz word, but I have done a couple sub-to flips knowing that I only needed to hold onto them a couple months and I was prepared to pay off the notes if they were called.Sub-to for long-term hold on the other hand has me nervous. 

I'm considering selling the property to have cash to look for a 2-4 unit on-hand.

You get tied up in court and every deal you've ever done gets reviewed to see if there are any other "fraudulent" transfers.

Lastly, if you’re currently taking a homestead exemption on property taxes, once that drops off (if you’re currently taking chose to transfer the exemption to your new home) your property taxes will likely increase $1k-$2k thus increasing your monthly mortgage.