Quote from @Sophanara Khoeun: As titled, I am new to the property rental scene.

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

It hurts the tenants ability to find another rental, nobody wins, and it takes forever costing you money. 

I am also willing to work for a more experienced investor or property management company in any capacity, be that market research, deal sourcing, property management assistance, rental optimization, or anything else needed.

Purchase price: $530,000 Cash invested: $100,000 My journey into short-term rentals began after years of investing in long-term properties, but it was a podcast that opened my eyes to the incredible potential returns of STRs.

High rental demand (Section 8 too).

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!

I wholesale some properties, and others make sense to take down as rentals.

@Michael Baum how many Short-term rentals do you manage this way where you are on call all the time?

My concern is doing the cash out refi on my other rental and causing a new and much higher payment on it that I can't just pay off like a loan.