Some states don't have an income tax and don't require a tax return filing obligation.Some states allow for bonus depreciation/section 179 expenseSome states don't allow bonus depreciation/section 179 expenseSome states follow federal guidelines for real estate professional status, some don't.

One thing you can do is after liquidating your holdings and purchase rental property, is do a segregation analysis and take all the bonus depreciation you can to offset those gains.

You may have exposure to some esoteric filing obligations which include FBAR, 8938, 8858, etc. 

Having some professional pictures of your property would be an added bonus. 

I talk openly and honestly with the people, I tell them the ugly truth, give them my cash price and a terms offer, where I can "risk" a higher price because they are mitigating my risk exposure. 

An added bonus is they're all right next to each other.Plus, there are other options besides buying and flipping properties.For instance, I love lease options because I can essentially negotiate the right to buy a property in the future while I rent it out now.

Either way, you save money and never have to deal with the utility companies (extra bonus!)

@Casey Powers my thumb rule is 1% rule to break even - anything more than that is bonus(passive) :-)

Things to consider:-NYC appreciation history, forced equity with 203k/Homestyle fix, Replacing my high rent with a mortgage (that tenants help), fixer upper experience with the rehab, proximity to work & family, MIP until refinance, ability to HELOC down the linevs-avoiding/limiting exposure to MIP & generating potentially more cash flow, possible need for PM, still paying my rent but maintaining my quality of life, still getting landlord/rehab experience but in a dependable market upstate.Any and all insight, suggestions, tips, referrals & recommendations would be greatly appreciated!

In this case, you might be better off creating a bonus room that could be used for a home office.