Ideally if you can find one that still has exemptions on it, you'll be ok for the next 12-18 months.

So I thought how about the education market - universities - not college students but rather graduate and professional students (e.g. medical students who spend 4 years in one place).Targeted tenants.   

The capital gains exemption is for single or married couples.

I am a disabled vet as well so I will be exempt from the VA funding fee as well as property taxes in Illinois.

If that's true, and you own less than 3 Homes, you are In Accordance with Federal Fair Housing Law EXEMPT from discrimination Laws.

I have a decent credit score (>750) but my brother has a much lower score (low 600's) due to some medical debt he incurred many years ago.

Is it education or medical debts? 

You may potentially be exempt under other Virginia law, but an attorney would want to read your Articles of Organization before confirming, and would largely be based upon who has the controlling interest.B) You may be opening yourself up to premises liability by not transfering the properties into the LLC.

I guess I’m kind of a late bloomer, pursued a medical career out of college and that has dominated the last decade of my life.

There is a delayed financing exemption if you purchased in your personal name and are looking for a Fannie/Freddie lender.