He is sleeping in so I don't yet know if there is an injury there that needs medical attention.

However, most states have an exemption for when the beneficial ownership has not changed.

If you sell one property that was your primary residence and you either rented part of that one structure out or you moved out and then converted it to rental for a bit then you would simply sell the entirety and take the full 121 exemption as boot and then then 1031 the rest. 

Like yourself my wife and I started investing after I finished with My electrical eng Grad school and she finished with her medical school.

Many areas have home stead exemptions that can significantly lower the rate. so what current owner is paying may not be what you will be paying.Also what is the valuation the taxes were figured against compared to new sales price. those taxes could raise significantlyYour insure estimate would be extremely low compared to my area in Georgia.

If I can and then sell it 4 years later, can I get the capital gains exemption when I sell it?

some medical benefits of marijuana : -1.

@Darren GregoryYour friend refers to a very old (and long dead) rule, which is why it's best not to ask friends for legal, tax or medical advice :)There are only two ways to control capital gain taxes on selling your own home, and they can be combined.

Also, considering his age, his medical expenses can only increase and he may need financial support for the next 10-20 yrs.

@Shar Rivera, most syndications outside of crowdfunding are done under 506(b) exemption which requires that you know each other.