Looking for a CPA or tax preparer that is well versed in the STR loophole and cost segregation.

Below is a quick summary: Generally, the four sources of return in rental real estate are:1- Cash flow2- Loan paydown3- Appreciation in value4- Tax savingsExamples of performance metrics and what they are designed to measure:- CoC (Cash on Cash) is a measure of net return generated by TWO sources (i.e.

Also seems like they like to stick on wealth taxes for rich greedy landlords and investors.

You can also explore Salem or bordering areas such as Derry or hereabout but they tend to be very high tax areas so that eats away quite a bit of returns and would not appreciate as well as more Boston central locations.

@Matt Lord there is no "right of redemption" for PA Tax Sales. 

That’s called a career change, not retirement.What you’re looking for are ways to generate income while you sleep.If you haven’t done this before, it can seem like a completely foreign concept.

WC is great - great schools, lower taxes.  

Before going into this, though I would be very conservative in your analysis of cost to renovate and what you think market rent (along with increases in taxes and insurance) would be so that once you are ready to refi into a longer term loan, your DSCR is rock solid and so is your cash. 

The third building is on its own piece of land with a separate tax ID.

Since FL doesn't have an income tax, go with a MA accountant.