Possibly i'd subsidize the tenants and make the increase when they move because the market will eventually increase rent to catch up with the higher property taxes.After making all those improvements, I would lean towards the long term and try to get as close as possible to break even now while at least slowly increasing rent enough for the tenants to cover the property tax increase. 

I think with some improvement on the house.

Lenders are seeing near a .50 basis point improvement in multi-family and mixed use loans this week. 

I definitely over improve the properties and I am sure somethings can be left as is.

I’m assuming the goal is to have your REI Cashflow pay for and keep up with, or even improve your lifestyle, way before you retire.

This allowed my clients to buy the duplex and then use the rental income to improve their financial standing, making it easier to qualify for future loans.

We would like to think that our love, REI, is populated with folks who want to get sellers out of a jam, lenders who want to see houses and neighborhoods improved, and rehabbers to do what they say and say what they do.

Hope I am wrong and the last owner got you some great quality tenants or that overall things have improved.   

I'm not sure that would improve your position by taking the tax/penalty hit (not sure of your age) you would incur by withdrawing money from retirement. 

The vacation rental certificate is similar to the City of Anna Maria and the City of Bradenton Beach; however, there are more documents and information required to be submitted, and the vacation rental unit and improvements must be inspected.