This in turned caused a dominion effect of other tenants wanting to leave.  

A nonpaying tenant, tenant caused damage, etc. 7.

Which caused a lapse in compliance. 

@Abel Eskinder since you're out of the country, you'll probably want to give some thought to our copy & paste info below:-------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

I was wondering cause my friend says the section 8 tenants have been hisd best for the past 15 years.  

I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?

That way, your records are consistent and they should never due something that causes you to reopen prior year taxes.

Last I checked prices are creeping but not making big jumps causing negative ripple affects.

@Robert Morris it can work - until it doesn't via a lawsuit.Challenges:1) They are NOT professionals2) They are not licensed, so may cause you legal headaches3) They won't have insurance, so what happens when their actions lead to a lawsuit?

Or buy a fixer upper and work on renovating (valuable learning experience if damage not too extensive) during college years then sell and keep up to $250,000 tax free profit as your primary residence allows.