Could I sell off the ADU or main house separately?

I agree that it is a lot of money up front, but if the norm for the area is first and last month's rent, remember that the tenants who are moving in won't have paid last month's rent to their current landlord (if they are from the same area). 

I’ve seen it plenty of times over the years, and I’d say you’re already ahead of the game for thinking through this strategically.

All of my porfolio is in the area.

I just received a quote from my AC company, these are the two options we received:Option #1: For a 2-stage Rheem heat pump system the total price will be $8,340.00.Option #2: For a single stage Tempstar heat pump system the total price will be $7,280.00.The property is a long-term buy and hold, so we plan on owning for the next 30+ years ideally.

About to close on my first investment property in the coming week, 4-unit in outside of Madison, WI.

I have been soaking up information from youtube, podcasts, websites, etc., as I am sure we all do, and look forward to taking the next step on this journey.

If you can't find the deals at the right discount, then maybe you can create the discount.Buy one and flip it. 

We wanted to keep access to the software but I believe they only go through financial planners though, which are broader services we didn’t need.

An option is to add someone else to the loan.