Staying out of the high crime and some of the extreme high end areas is our goal, supply is low right now, but plenty of deals to be made especially for those that are house hacking, or have skills such as rehab experience.

Stay in touch!!

You get tax benefits while you stay there, and if you sell after two years you pay no capital gains.

I have run the numbers in the Calculator it looks like it will pay for itself if it is rented an average of 3 weekends a month (minimum 2 night stay.)Thanks,Adam

If there other income is 30K from SSI, it seems that they would stay in the 12% tax bracket top of about 77K. 

I'd stay away from regional or national banks to be honest.

We did not agree to liquidated damages for early termination - given the exclusive nature of the community, the extremely high commission cost, high property costs (taxes, HOA, etc) and the fact that it can take anywhere from 3 weeks to multiple months to rent it out (at high carrying costs) - we depend on stable multi year tenancy for the numbers to work out.It’s critical that when the tenants renew, they stay for another full year.

Like I said, I currently live in Chicago, enjoy it and would rather not pay rent, but don't know how long I will stay here. 

I had a couple friend that were looking for a place to stay after college as well and my girlfriend at the time was out of state, I thought what the heck this house is way to big for just me.

Couple of options perhaps1) Look elsewhere where you have boots on the ground in cash-flowing markets 2) Pursue off market deals - takes a lot of time and knowledge though, you sound like a busy professional3) Live-in house hack - that's if you were staying longer though, if you're forced to move and your rent doesn't cover expenses and the cycle ends, you're stuck