We're considering selling the property due to challenges of long-distance management.We're still interested on investing out of state and plan to gradually scale our investments over the next few years, focusing on areas close to Illinois, like Wisconsin or Indiana.Any suggestions on how to approach selling our multifamily property and buying in Wisconsin or Indiana in the current market would be greatly appreciated.

Last thing you need is a spec house sitting on the market too long.

All of those are "part of doing business". 3 years, 7 Airbnbs and hundreds of guests later I'm still a proud host and a big fan of the mid-term / short-term model!

I know that many in the bigger pockets community are more the DIY type and self-manage, but for those of you who have used property managers for your short term rentals, what have been the pros and cons of your experience?

Best bet is to contact your trusted lender or other financial institutions to compare offers to find the best interest rates and terms that suit your investment strategy.  

Also, I'd think about the long-term potential for appreciation and the health of the neighborhood.All in all, I think it's great that you're at a position where you can seriously consider investing and wish you the best of luck either way you go!

Those costs factor into the investment and I think technology is going to go a long way in reducing the costs for vendors, lowering the costs for buyers and helping Roofstock bring about a better experience for the investor.  

How do you estimate just how many residents will stay long term vs. decide to leave or perhaps pass away during their stay?

Hi Danielle How long has the property vacant for? 

The core 4 is David Greene’s long-distance investing strategy and consists of a realtor, contractor, property manager, and lender. https://www.biggerpockets.com/blog/core-four-real-estate-tea...