Usually the first few years you’ll get a paper loss, so no taxes to pay, but once you show a gain you’ll have to pay.

I am having difficulty figuring out how to use the numbers here to see whether i cut my losses or proceed knowing some major capex work could be done after renovation, so hopefully no major expense in the near to medium term, and all the potential of the area in price growth and rental growth.  

First, it's a plan-z measure, that if they have to take the asset back, that after all the expenses of such and what-not, there potential losses are mitigated to $0 or as close to $0 as possible.

Hi Bruce, the calendar is good for a high level vision, but you're right, it's not so easy to check all auction dates, find listings, and keep track of current investments, that's why we developed fastlien.Every day you can see the listings you are interested in and all related information, plus a lot of other things :)I would be very happy if you try the SW so I can get your feedback, you can just try it for 7 days for free.

If it is due to a condition of the property (multiple losses, unrepaired damage, etc.) it will be more difficult to get a regular company to write it. 

The amount was based on the possible loss we can incur.But we are not taking in charge the current eviction.

In my mind, a multi-member LLC where my wife and I are 50/50 partners make sense, but I don't know if that will cause problems at tax time with counting losses from the LLC against my active income.

You would go right to QuickBooks and pull your Profit & Loss and Balance Sheet.

Allstate and State Farm in Illinois lately have been huge a**holes as far as providing coverage when a loss occurs.

So I take what you have and what you expect, estimate the time it would take in a whole year of work and create my flat rate.I notice short term rentals are about 1 hour a month of work per property, since we need to track each property's Profit & Loss for Tax time, this is also tracking a mortgage and depreciation as well for that property.