If you are worth say 300k and taking a big chance with a good amount of money down then stay away from the low income areas and pricing. 6 to 7 years ago my friends were buying properties for 55k cash in Roswell in A location and putting 10k in to make rent ready for 900 a month rent.

But I stay around $625/month and I get the same tenants.

Stay away from HOA's. 

@Spencer Harvey I know people have reasons for why they prefer a HELOC but I tend to stay away.

So call a few times (not too many) be super friendly (remember, this is small town lending) and stay patient!

From what I understand, I should be ok if I list the property as "xxx and yyy, trustees of the trust, as MY sole and separate property",  then the ownership still stays with me and my social security number, even though it resides within the trust.   

I’m gonna stay for a couple weeks cause I wanna drive around and analyze everything.

With the university of Chicago nearby, it should stay booked. 

If it's only a year lease perhaps the least painful thing is to let her stay through her lease and then give her notice 60 days before the end of it that you have other plans for the property.RE marital status, FWIW, I sometimes misspeak and call my ex "my husband" 8 years after our divorce.

Many tenants will stay during the inspection and you will get to meet them, shake their hands and see what you are getting yourself into.