If you're willing to trade the time and effort, your best shot is finding a deal yourself... but remember, this requires experience and skill as well. 

But I do things that are rarely recommended--- like trading work (mostly low skill work) for rent.

But, I have been tempted to sell/trade up out of boredom, or a need to feel like I’m actually involved in the business.

I have found a few run-down vacant homes; the owners owe a few years in taxes. could i offer to pay the taxes for them in exchange of the house? would that be a different type of contract from the typical wholesale?

For the passive investment you described, UBIT would generally not apply based on equity in an active trade or business, though you should ask the syndicator about whether the investment is likely to generate UDFI for an IRA.

I am an  HVAC Technician by trade.

You could hire different professional trades and pay them for their time to inspect the property.

Since then i have also realised that cryptocurrencies and stocks can be traded with the help of technical analysis.

Still working on building my bench of trades, so that I can have dependable people running the day to day operations.

The thought was that we should be able to cut him a 1099 at the end of the year for the revenue he will be bringing in, but neither my wife (an accountant by trade) or myself (software developer) have had experience with this before and don't want to get stuck not being able to expense all of these costs.Please advise, and thanks in advance!