Cash out would take me from a 7.25% rate to 8%, which is a few hundred dollars per month, and they will likely make me wait all through March to do the cash out to meet seasoning which is another $2400 interest payment I could avoid if we could refi by the end of this month.

Ok, now let's look at where the Rubber meets the Road.  

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

It has a free plan that I think will meet my needs.  

Looking forward to meeting others in the area. 

@Marc Zak Using an LLC for each property provides strong liability protection by isolating risks to individual assets, with income and expenses flowing through to your personal taxes on Schedule E.

As long as it meets "minimum" size standards it can look like a broom closet and be considered a bedroom... ridiculous, but it's out there, and in a tight market people will pay for it... 

Happy to meet for lunch sometime and talk about how we can help each other!

Be mindful that there are rules that the lenders want you to check off.Furthermore, there are other rules on the tax side where you want to normally be under to get the most tax benefits.The magic number in both instances is '14 days'Lenders want you to stay atleast 14 days to meet the secondary home requirement.The tax accountant normally wants you to stay less than 14 days or 10% of the days it was used as a rental to treat it as a rental and not as a personal residence.Best of luck!

The best approach is to set clear, written criteria, and then price the property at a rate that gets you enough applicants that you can find a few who meet your criteria reasonably quickly.