Raw land not actively developed is always considered an investment.  

Anyone out there who has taken a DIY approach to REI (ie not through turnkey companies) and is actively investing in 3 or more markets (meaning not just holding rentals from once upon a time but still looking and buying in at least 3) care to chime in?

Let me start by saying I’m not a cpa so this isn’t tax advice, go consult a cpa.From my understanding if your AGI is above 100k they start phasing out how many losses you can take (capped at 25k if you make under 100k), once you hit 150k then you can’t take any losses.The only way (I’ve seen) around this (assuming you’re married and you file jointly) is to have one of you be a “real estate professional” which means you spend 750 hours a year working actively on real estate and that you don’t spend more time than that on any other job.If you meet that criteria you can take unlimited losses and use that to offset other income, so in theory you could make say 300k and show losses of 350k and pay zero income tax.

Seeking out an attractive investment opportunity in NYC is extremely hard and huge entrance barrier for someone who doesn't have too much money.

@Laurie Chimento  you will have to seek a portfolio loan for the "Loan to Value" (LTV) percentage you are seeking. 

As far as license for wholesaling like @Chris Heeren said, its gray, the terminology that dictates what activities  require a license are (for a fee and for another) and a fee is described as compensation or a thing of value, so it doesnt have to be money.

Then 10-15 days later the mother and father went in and started seeking medical treatment for carbon monoxide poisoning.

Keep up the great work of staying active on the site and letting the knowledge soak in :) Best of luck to you! 

@Stephen KunenProviding substantial services to your hosts provide suggestions that you should report it as schedule C as opposed to schedule E.Substantial services include but not limited toConcierge, meals, housekeeping, cleaning, entertainment etc.A pro of reporting it on schedule C is that losses are deductible and not subject to passive activity rulesA con is that income will also be subject to self-employment taxes in addition to income taxes.

You want to try your best to target those sellers and seek them out.