Now, you need to figure out how to find deals and pay for them.

We explained to him we would pay for probate and pay to fix up the house to get it rented.The lease is for 5 years but dissolves once we close.

I currently live in a 1000 sqft home that we pay a mortgage on.

It'll take time but can really pay off if you stick with it.I'm in Los Angeles and I've investing in TN and GA in the past, and currently investing in SE Wisconsin (your area).Let's connect and discuss the market.

In return, they will be motivated to get a job and pay back every dime owed while lavishing you with praise.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

@Jon D. some questions, the answers may help you better focus.1) Why did you pay your primary mortgage off in the first place?

This allows you to use all of the tax and deferred depreciation recapture to purchase the larger MF propertyA consolidation exchange is where you sell multiple investment properties to purchase a larger and nicer investment property, but you also get the benefit of using all of the tax you would have had to pay to your advantage.

If your willing to do so, you can live in the casita and then rent out the main home and have your tenant pay the majority/all of the mortgage (depending on what type of deal you find obviously). 

Pay your attorney and your CPA for a customized advice.