The problem is that by the time I close, it's late September and I won't ready to rent until November/December which is not the optimal time of year to be looking for tenants.

Is the cost to paint and maintain the painted brick worth the investment vs leaving natural?

Clear accounting maintains friendships...

They will fail to pay the bills (including rent to you) on time and regularly, they will fail to do the yard work, they will fail to maintain the interior and make any necessary repairs that come along. 

The current tenant has been living and maintaining the property.

Some things seem intuitive, no one ever there, house in disrepair, yard hasn’t been maintained, etc, but I’m guessing there’s probably a lot more I don’t know to look for.Thanks again!

Perhaps they're an out-of-state investor who just wanted a rent check without the responsibility of maintaining the property.

In my experience, multi-family housing can be optimal for both investors and renters by offering a tiered approach to different levels of income - small apartments, large apartments, townhome apartments, and high-end dwellings.Most renters aspire to have diversity in their community and in their lives.

Between deployments and having been stationed all over the country, remotely purchasing and maintaining properties has its challenges but I am now in Columbia, MD and only a 7 hour drive from my properties.

The goal is to set up an investment structure that optimizes the level of taxation given the aforementioned context.