@Eric Lee Nation    I did ins claims in another life for 14 years - I do not recommend that EVER as someone's employment but I did learn a few things.Here's 2 things agents or no one will tell you -- your Replacement value (RV) on the house is JUICED up way higher than what's realistic -- however you have a relatively inexpensive house so it's not much of an issue - but typically the reason they juice the RV is to get your wind/hail deductible higher -- typically 1%, 2%, 3%, 5% of RV is what your wind/hail deductible will be even if you had a $1k or whatever other deductible they offer for any other peril -- so follow me for a minute - you bought a rental for $150k -- they've juiced the replacement cost to $250k the most likely loss in KS or the midwest in general is going to be wind/hail --- the math actuarial nerds do this so the casino or the ins company in this case has the upper hand -- do the math what a 2% or 3% deductible on a $250k house will be -- I have a commercial building insd for over a million -- the lowest wind/hail ded they will give me is 5% -- the only reason I have ins at this point is I'm required to -- the wind hail coverage is worthless to me with as high as the deductible is.Anyways with that out of the way - ask your agent if you have a 3% option - at that RCV cost they figured of $99k that wouldnt be much different than the $2500 all perils coverage you have now -- Also I'd wager as someone mentioned dropping the med payments to others coverage -- it probably wont make a bit of difference in your policy cost -- I could be wrong - but I'd guess $25-50 dollars a year -- your coverage is the price it is due to the perceived wind/hail risk the company is putting on KS.I'm with Big Red and have been for a # of years -- your price to insure that house is on par with what I get from them for that replacement cost -- though i think State Farms game is a bit different they really jack up the Replacement cost so I have higher wind/hail deductibles -- I'd make out good if the house burnt down or a tornado destroyed it - but for a hail claim there wouldnt be much there.

When I first started I was also convinced that I needed to have 3rd party property management, and I looked for my first deal accordingly.

I know every partnership is unique and it really just depends on the two parties involved, but having the general opinions of other investors will help us to understand more about what we should or should not expect. 

The lease document is there to protect both parties.

I know, it’s rude of me to do such a thing, but had no better idea what to do.Well, the thing is that the guy owes to his bank thousands of dollars as he kept depositing money to various online casinos.

A qualified 3rd party intermediary makes everything easier (also required) and if you don't have another deal or property lined up or in the works it makes the process 10X more stressful.

I've read conflicting information about what triggers you to have to pay self-employment tax on your short-term rentals.There seems to be a consensus that the following does:Airport TransportationProviding cooked mealsOffering ToursCleaning during the guests' stayDecorating the property for a party as a serviceI'm not sure if these would cause me to have to pay self-employment taxes, as I've seen these items on a couple of lists but not most:Providing a coffee stationProviding a welcome basket with food itemsProviding bikes and kayaks for the guests to useDoes anyone know where the line is of what you can and cannot do and provide?

At that point all parties new that I was serious about the deal.

When going after damages you need to prove that you tried to mitigate damages (i.e. relisting it with the intent to rent to another party).  

What did both parties do exactly?