Irrespective, don't go over what YOU determine you need to pay for a property, I've seen people increase their purchase price more and more just to be competitive and get the deal, but then they end up eating into their profits and barely make money when they go to sell.Anyways, I hope everyone in Chicago is staying warm today..! 

I am currently in the process of filing my 2015 tax return (extension) where I can remove those expenses to increase that year's self-employment income, but that income would be taxed at the 28% bracket so not sure if it's worth it. 

I've just started this year and am finding the MLS increasingly difficult to find anything that pencils out for a long term rental.

I would now like to seek some professional guidance from an architect, residential construction contractor, etc. to first gauge whether or not my vision is possible, potential road-blocks, and alternative development ideas.

For the past 9 months I have been listening to and reading BiggerPockets material to learn how to generate wealth using real estate. Based off of what I have learned I think the following course of action is the best ...

The plan is to increase to market after 6 months.  

I've never negotiated such a deal so I'm seeking any advise. 

If they're 10 year tenants, you might have an opportunity to increase rents as well! 

We had our second home rented out before the closing.At this point and after reading numerous books on real estate, I realized that although we had reached our goal of owning a rental, our finances were completely vertical and I need to spread out to increase cash flow and reduce the impact of a vacant property.In January 2016, I started data basing different markets across the USA.

You can google "We Buy Houses in LI," call bandit signs if you see them, go on Craigslist and seek out ads who are looking for properties, or even post an ad stating you'd like to work with investors to bring them deals and locate investors that way.