Where I live is extremely expensive and pay is not up to par.

Bikes from a bike shop will be more expensive but they will be assembled correctly and will have fewer issues.  

Running Google ads ("Sell my home fast or for cash") or Facebook ads targeted to motivated sellers is an expensive way to generate business, but also can work.

If you definitely wanted to be in Manhattan, then condos are the way to go - however they're generally more expensive than coops.One thing I've noticed with existing and past clients is that apartments in NYC don't tend to appreciate too strongly, unless you're buying something with 2+ bedrooms.

Even the most expensive market, even the most depressed market.

If you're living for free with parents, that's a different story, but if you're saddled with an expensive rental, converting that cost of living from a liability to an asset is a great move.

You want your accountant (tax preparer and/or bookkeeper) to understand how to classify your business items - fundamentally, there are just 5 categories of entries (asset, liability, equity, income, expense) and the transaction is booked as a debit or credit to the appropriate category.

Paying for taxes because of a misfiling will be more expensive than just getting another CPA.

I'm planning on house hacking (honestly comfortable renting out bedrooms in say a 4-5 bedroom house) and having that cover all my expenses. 

I believe there are less than 1,000 people in this country who earn more than $100K in profit wholesaling over the last two years, and even that's hard to accurately pinpoint, because most wholesalers, excluding the folks who sell expensive courses, tend to have larger holistic real estate businesses, that include flipping, hold, private lending, turnkey rental sales, construction, and other related businesses.