The experience you'll gain on the first deal - and the desire to do it over and better again - will likely far outweigh any heartache or stress from the process.

The insurance company would not likely try to subrogate (more accurately deny) the landlords claim as the negligence of the tenant far outweighs all other factors. 

But the pros far outweigh the cons IMO.  

Devon:Lots of questions and you would be best served having a chat with your accountant and attorney before heading too far down this road.When you are just starting out, the overhead (accounting, reporting, fees, taxes) of such a corporate structure probably outweighs the benefits.If you hold a rental property within a company (CCPC), the revenue is consider passive and is ineligible for the small business reduction afforded to active income - hence, the company will pay income tax at the full corporate tax rate.  

We currently live in CA and own in TX and our experience has been that the benefit of no income tax far outweighs the higher property taxes.

There are lots of boarded up homes that turned out that way because a landlord got underwater quickly on a home in a tough area, then had to rehab to get the place on rentable condition and the rehab out weighed the total value of the home.Good luck!!

Outweigh the profits to the cost, to the effort of keeping it, maintaining it etc. etc.Keep in mind, many investors would die to own a money generating quad.It also depend on what your goals are.

Just keep offering help and hopefully the good outweighs the bad.  

But if you can afford 15% or 25% down on an investment property, the downsides of down payment assistance outweigh the upsides anyways. 

The potential downside outweighs the upside by a lot.