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.

I know you have to stay in a home for at least a year with an FHA loan, but I'm not sure the terms for buying another property after that year and keeping the initial one.Any thoughts are much appreciates!

What is the order I need to get this done to stay on the up and up ?