Being close to expiration I’m going back and forth on what to do.This tenant has just been a pain.

I will say there are a FEW wholesale lenders that are a pain to work with but it comes back to the rep not knowing or the lender taking their sweet time to review a file.

I unfortunately feel 100% of your pain

I love it for the guaranteed rent, tenant stability, additional accountability with the housing authority and large demand for Section 8 housing without enough supply.With strong screening, I'm able to find great tenants and Im not owed any rent.Cons you will often hear is that the tenants are harder on your properties (doesnt have to be the case in my experience if you screen really well), the Housing Authority is a pain to deal with (this depends on a couple things - how well run your local PHA is and how good you are at handling process & details) and the extra inspections/red tape make the niche unprofitable (see what I said above about Housing Authorities).Done right, I believe Section 8 is one of the most stable & profitable. 

Those all seem to be common pain points for owners.

In other words, if there was a broken leg on your property that resulted in $250,000 in medical, lost wages, and pain & suffering, if there was gross negligence on your part, the total judgement could be $1.25 million, and worse, your insurance company could deny it.So what constitutes gross negligence? 

Just painful to think about.

examples:Baltimore - a path to never-ending pain (biggerpockets.com)Experience of OOS investing in Cleveland after 1.5 years.

Sorry I know this one is going to be painful for many rookie investors just getting started who want to live on the beach with their mail order cash, but this is not they way investing works. 

If I'm investing out of market, I want to be sure the location isn't a pain to get to.