@Sri Reddy it all depends on your goals.

It really depends.   

This would depend on whether your property is overvalued by the tax assessor and in turn you are paying additional taxes on that additional valuation.

While this is municipality dependent, if the contractor is not licensed you likely cannot obtain the necessary permits and approvals.

I think it will also depends on state laws and a lot of information not present but the HOA rules and insurances are two different things.

That will be an important piece to this depending on how you plan to source your capital.

Whether the lender decides to do anything, and exactly what they decide to do depends on the lenders particular strategy, target ROI, risk tolerance, current interest rates, interest rate of subject mortgage loan, etc. 

I understand that if you live in a state that does not have a state income tax - you won't have any state tax liability, but based on $110K income, you would be in a 24% federal tax bracket...Distributions from an IRA or Roth conversion would be considered ordinary income and subject to ordinary income tax; capital gain tax is not applicable here, so I'm not sure why you are bringing it up... 

It's not what I would call a super rough, probably different street by street, and would most likely depend on the neighbors right around the property. 

Providing relocation assistance to tenants, for example, if I want to sell the property or move back in - this can range from one month's rent to thousands of dollars (e.g tenant has a disability, minor children, elderly it will cost you more), depending on the city.