I did own, renovate and sell a primary residence here in the US and managed to get an exemption of FIRPTA in that case but its not something I'm willing to take on without a green card residency status.

I want to sell it to my brother for $250k.Will I still be exempt from capital gains tax 2/5 years if I sell it to my brother?

Here are the details:2 bed, 1 Bath, detached 1 car garageAsking Price: 35kFair Market Value: 55kRent: $600/mo (although i believe this property could demand higher)Property Taxes: $66.24/mo (Has an owner occupied exemption of 6k.

You need to live in the property 2 of the previous 5 years to qualify for the capital gains exemptions.

If you haven't yet lived in it for two out of the last five then you should be able to pro rate the gain allowable by the number of months you have actually lived there by virtue of the change of employment exemption from sec 121.  

Title insurance will exempt it if it exists prior to closing, and won't cover it if filed after closing.  

That would've lowered your parents cap gains and you would already have seasoning for an owner exemption on the 100k gains you hope to make.

I would write in clauses that had the tenant waiving their rights to notices, waiving their right to their "exempt" personal property that could be attached, etc.

RandyOf course the people that make the laws are going to exempt themselves but as far as I'm concerned their right to free speech is no greater then mine.

TRELA has a statute that lists the exemptions from licensure and it usually includes owners managing their own properties.