If you are using rental income and you already filled your taxes with those rental properties then they will use the your tax returns and schedule E to calculate your income.

I would talk to a qualified intermediary and a tax professional.

Essex and Hudson county are blue (high property taxes too) and I would never buy there. 

I know the cash flow is weak, if not potentially negative, once insurance and taxes are included and that may immediately make it a bad deal for some investors.

Having a prior claim within the last 24-36 months is a red flag / non-starter for many carriers at the moment especially for water leaks.I advise all my clients do not play go fish with the insurance companies right now unless you 1.

The idea is to get is much out as low of tax rate as possible.

Here's why.People are drawn to our area due to the absence of natural disasters, low property taxes, home prices close to the national median, and a thriving tech and research hub, coupled with the life sciences sector.Considering the ongoing influx of people and the likely rate adjustments announced by the Fed for later in this year, we anticipate prices actually  rising as buyers enter the market.

The downsides are you’re paying taxes that will go away at their passing.

Tax rates are very high level, so you will want to adjust that as you pick a more specific location to model out.  

My question is would it be best to build the casita prior to pulling the cash?