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

If you keep your X flood policy, you will stay at X rates.