I would recommending looking at your property through the eyes of the NBA, or Next Best Alternative, to see if there is a market for you property as a mid-term rental. 

We are newbies, and don't want to miss out on a great investment and tax savings opportunity, but obviously want to do everything correctly in the eyes of Uncle Sam.

I am also eyeing Abilene as a potential first investment market.

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!

@Peter Nikic Thank you for response, when the time comes- I will be looking for a property manager, I’ll reach back out to you then..Catskill, NY -currently on the verge of breaking through -similar path as Hudson,NY - keep your eye out !

Learning the ins and outs while keeping an eye out for a great deal is a smart approach—knowledge and patience go a long way in this space.

Yea this is a long-term personal play more than a strict STR deal. 

If your Realtor is anything like me, they want to spend any marketing funds where the most eyes will be. 

It’s always interesting to see how people’s backgrounds play into their investing strategies.What kind of multifamily properties are you eyeing right now?

If you’re a homeowner thinking about selling, keep an eye on mortgage rates.