Failure to pay penalty - generally .5% of unpaid tax balance.Both penalties can be waived if you can produce reasonable cause. 

The gutter anchors have pulled out of the CMU wall causing water to leak through the CMU wall.

I remember with a previous business I had my car insurance agent told me that I had to add something to my insurance if it was now going to be advertising a business- and if not It could cause me coverage issues in the event of an accident? 

This is not to blame that the tenant caused a situation for condensation but it is for not reporting issue in a timely fashion which could have allowed fixing and minimizing the effect.

That said, if you have terms in there around owner-financing, etc. that could be a cause of reluctance.

If you have decent credit and this is your first house, I'd consider being an owner occupant for the first year and buying another as you get more into a career.There's some pretty cheap investments around here, but you gotta watch out cause there's crap too.

Hoping to find a company that does direct lending and 100% of the servicing (cause working with a billion companies after the deal sucks) but I'm not holding my breath. 

There's a lot of ways you can approach this, but keep in mind just cause you get into wholesaling doesn't mean you can't then give buy and hold a try, and vice versa.

Make sure you clarify what will happen if they don't fulfill this duty.Here is an example from our rental agreement:1.LANDSCAPING/YARD CARE.Regular landscaping/yard care (mowing, edging, trimming, fertilizer, weed control) will be provided by _______________________.For all Tenants:a.Tenant agrees to keep yards, walkways, patios and decks clear and to keep premises free of junk and debris.b.Tenant accepts liability for all landscape damage and/or replacement of such, if caused by neglect, abuse or lack of water.c.Tenant may plant the beds adjacent to their dwelling to their liking, but only with those plants that are of appropriate size and type for the beds.All plants brought or caused to be brought to the property by Tenant will be cared for by Tenant.d.Tenant agrees not to cut or prune trees, hedges and shrubs.This will be Landlord’s responsibility.e.Tenant agrees to properly dispose of all plant debris and agrees to not leave such on the property.f.Landlord will consider special Tenant requests for planting and removal of plants, shrubbery and trees, but reserves the right to determine the make-up of the landscaping.For Tenants of single family homes only: a.Tenant agrees to mow, water, and keep the grass, lawn, flowers and shrubbery thereon in good order and condition, applying fertilizers and weed retardant as needed. b.If there is a failure of Tenant to keep the landscaping in good order and to follow these guidelines, Landlord reserves the right to hire a landscaping service at Tenant’s expense (after a 10-day notice to perform covenant).c.Landlord reserves the right to restore the landscaping to its initial condition, as it was at the time Tenant began occupancy, or if improved during Tenant’s occupancy, to the level of such improvement.

There are simply too many ways you can market to someone (cause that is really all we are are marketers).