You usually pay less in taxes and you build your portfolio much quicker than taking that money out. 

That’s the key benefit.As for the cost segregation study, whether or not it makes sense really depends on your tax situation.

Do you have an idea of the total tax credits?

Nothing over any service you wanted to provide.Do property taxes fluctuate?

My question is this, can I deduct my passive losses that occurred in 2017 on my 2017 taxes or does it get rolled over to 2018 because my income is too high?

Any taxes or other issues that I may run into down the line?

You will truly be raising the clock, as each day will cost you very significant money.  12% interest on $250k is $2500/mo, or about $80 per day in interest, not including your other carrying costs (utilities, property taxes, insurance, HOA). 

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.

$15k co-host, $6k insurance, $34.8k P&i (7%, 30 year DSCR), $5.5 prop tax, $12.7k utilities (mostly propane & elec), $7k maintenance/cap ex (3100’ with class A finishes), cleaning $24k (8 turns/month), then the small items. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.