Consider the trade-offs and best of luck.

I own my holdings through a publicly-traded mutual fund (there are many to choose from).

You could argue the the activity is not regular and continuous enough in order to be considered a trade or business, so it would be a capital gain.

I've traded a car in before with a transmission that was hit or miss and crossed my fingers that they wouldn't realize it. 

We were all young and dumb, but you balance the scales by educating yourself and learning the tricks to the trade.

Trade your work ethic to gain experience, but I wouldn't pay someone $1000/mth. 

Why do you want to trade a loan with lower interest rate and lower mortgage payments for one that is higher in both instances.I think your Cash Flow may be a little optimistic.  

I'm currently an Engineer by trade, working 3 nights per week, so I will use my days to work as an REA until I make the full transition. 

As for permits, I did put the wrong amount, after checking with the city, based on our estimated repairs it'll be $865 for permits + $250 for the various inspection visits (middle and ending visits as well as various other inspections for certain trades like roof). $200 for a permit would be great. 

Just curious to know what it would trade at.