That being said if you're projecting out you should also consider whatever market rent is since increasing rents to that figure may offset the tax increase. 

What is preventing me from moving forward at the moment is the contractor part.For example. if the advice I receive is that in order to enable a good flip i would need to be very hands on and that contractors are hard to find , I would likely avoid a more aggressive project like a multi shell.I am looking to flip and hold the first property with the hopes of getting an attractive entry point for cash flow.

Makes it more attractive.

During the election, Florida also voted to require a 2/3 majority vote on any tax or fee increase proposed.

In an effort to increase awareness of this important issue, defendants also agreed to place over 60 postings on Craigslist informing other Craigslist users that the Attorney General monitors Craigslist for discriminatory advertising and that it is against Massachusetts law to state a discriminatory preference against families with children or against recipients of housing assistance subsidies.http://www.mass.gov/ago/news-and-updates/press-releases/2009/ag-reaches-statewide-settlement-with-20.html

I know this isn't quite applicable for you yet, but you can also speak to your CPA (the biggest impact route I've taken) about how to increase your reported taxable income. 

A private lender can charge higher interest rates than the bank and thus increase the income derived Understanding that there is no guarantee in the real estate industry, and there are risks, a private lender can receive a return on investment of as much as 10%.

The house will be paid off in June of 2026 and my plan was always to pay it off, use the increased cash flow from no mortgage to pay down other properties for a few years, and then sell it and 1031 into something closer to me in Cleveland. 

If your losses are locked up by high income - then there is no point trying to increase them.

Great tenants, want to keep this one.four properties on a business line of credit, interest only, the interest rate just increased to 6.5%. owe 200k, monthly payment around $1,074.