Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

That's why mature investors with long positions like Boston while places like Brockton and Holyoke are more affordable.

You will never get that back in terms of additional cash flow

Start to evaluate deals based on the income approach and you'll do much better long term investing. 

Quote from @Peter Firehock: Introduction:Well you've certainly put together a long and comprehensive analysis.   

You can shift your perspective to enjoy what you're doing, yet reap the long term rewards by planting the seeds today. 

@Muhammad Kashif Flipping a property in 6–9 months results in short-term capital gains, taxed as ordinary income (up to 37% federally, plus NJ state taxes up to 10.75%).

Find out what financial problem you are trying to solve in the short term until your able to get to more "long term" problems that real estate helps with 

@Parmesh P. there is no such TDA paying 7% or even 6% long term,5 years or longer.

Depending on what you are trying to achieve, there may be some other lenders I could suggest.