It's great experience, and the more you can do it while you have a steady paycheck, they less painful the lessons-learned are financially. 

I think you can deal with it yourself, but it's really a matter of perseverance and pain endurance - depending on your relationship and feelings towards them.. 

Very similar house to the one I was visiting, cookie cutter neighborhood.I have some cash to put into the house to make the LTV work, but was also considering taking equity out of a house a few blocks away that I own free and clear. 

I have already approached them about it and it appears they blocked my email.

It is not that much more of a cost for permits but it does become a pain paying the fees.

It always pains me to paint wood, but sometimes necessary.

For example, when I get a 3,4,or 5 day block between weekends, I need to be able to lower the rates to attract someone or it sits empty

I've had a few where it's worked out but overall, the are a pain especially for tenants:I've had rejections for dishwasher that no longer cleaned, due to there was not actually anything broken.

Indianapolis can vary block to block though so you really need to know the areas well.

If it's painful that's good, because you won't make those mistakes again because when you see that red flag and think "well, maybe I could..." or "yeah but this is different" you'll remember that paper and go oh yeah, not doing that again.