I am similarly in the same location dilemma for my next investment -- to stay in Chicagoland, or look to Wisconsin or Indiana for better opportunities. 

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bp The second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.

It would be in high demand for a week or two a year, but I wouldn't think many people would be looking to stay in that neck of the woods at an AirBnB outside of the week of Derby.

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bp The second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.

The fact they are complaining online might be an indication the property manager dealt with them properly so be sure to ask the manager for their side of the story.I hope this basic guide helps.

In the past, I've stayed away from partnerships because I have seen them go sour, however, I feel good about the current prospect and can see the value he brings to the table. 

Most of them I've seen marketed are way over-priced and I'd be curious to see how well the were rehabbed and how long the tenants stay and how long the properties actually perform. 

But I learned that the work really doesn't care who does it, as long as it gets done, and eventually I became a rather good handyman and parlayed that into DIY landlording as a way to break into the market here.If you're determined to stay in Boston, I cannot recommend getting out to local real estate associations and talking to other local investors highly enough.

Lock in your money now and as rates continue to rise you'll see more and more rentors staying in the rental market longer.But beware because the rising interest rate climate could change quickly and with a correction we could see govt policy in a heartbeat that reduces barriers to borrowing and ownership. 

They can STAY and get their other deposit money back, there is no gun to their head.