Without checking the title yet, My question is, should I still possibly pursue it under which circumstances?

But, they're fraught with little nuances that depend on your circumstances.

Every area will have its own distinction....like NY/Boston/Chicago etc there may be A properties that are 100+ years old and there may also be brand new to market assets.

Facts and circumstances may vary! 

However, consulting with a tax professional or cost segregation specialist can provide personalized advice and help you determine if a cost segregation study is worthwhile in your specific circumstances.

If you buy at 50-70% of market value, you're hedging against downturns or unforeseen circumstances.

It's not necessary in all circumstances, but usually makes sense.

Seems like the wise move for those unforeseen circumstances that can happen.Love the firm NO on the HELOC option as well.

But before you rush your decision, you need to realize one critical distinction: treating this transaction as a business allows you to deduct all business expenses against this income.

However, given my circumstances, I will not be able to manage STR on my own.