We do not subtract $2k in taxes from our $10k contribution.

Well, if cleaning is $275/ea and you have 60 turns in the year, you have to subtract $16,500 from "what it makes" since that money goes right through your hands.

Interest expense - when modeling this in, I would take 50% of my interest expense and subtract out of NOI and the remaining interest expense I would be able to model in as a deduction at my marginal tax rate?

Then you take that number and subtract your mortgage payment from it.

I understand the process of finding ARV and then multiplying that amount by .70 and subtracting repairs cost to determine the amount an end buyer will pay for the property.

I got these numbers by subtracting 15% management fee rather than 10% in case of extra costs. 

Subtract your purchase price from your net sales price and you'll get an approximate idea of what your gain really is.If your profit is truly $400K over the $500K allowed by law then I think you're on to a great plan - move out, turn it into a rental, establish your intent to hold for investment. 

So, that would basically add the Florida room as an amenity, on the appraisal (adding between 10-15k to the value of the house - per your appraiser), and on a different line, they might subtract a $2k (WAG) cost-to-cure, to account for adding AC to that room.

Most hard money loans are around 12% or more, plus the point costs so that subtracts from your profit as well, on the plus side the loan payments are interest only and with a Wholetail you should only have the loan for a month or two.

If you get started out right it is not that hard to do the taxes in subsequent years unless you are adding/subtracting rental properties.