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.

I am exploring other options of partnering & owner financing through a private cash buyer, etc. but my goal here would be to use the equity I have in my single family to purchase an owner occupied multi. 

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.

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.

I would say about 1 lead per month 2 if I drop off the first 3 months of no activity.

We are exploring the idea of converting part of it into an community garden for a number of years until we have enough created enough capital through flipping to possibly develop the land. 

Although, it seems like a lot of effort to only make $500 or so bucks a month on a rental, well, at least if you consider that it's a much more active affair than buy/hold REI. 

We don't have a ton of inventory in that class, so it's a good idea to explore what is available and see if it works.