Report the full $100k otherwise you might get a matching error from the IRS.

These strategies require professional guidance, unless you prefer to receive such guidance after the fact from an IRS auditor.

If not IRS will charge it for you.

(All this also assumes a free and clear property - if they have a loan there are some other considerations - but still a perfectly doable deal).The (previous) owner would claim the interest portion of the payment as income - IRS form 6252 should be used for this type of transaction.We recently did an owner financing deal with a couple in their 80's for a 30 year fixed loan. 

NOTE: there is no hard and fast IRS rule about how long you need to hold a property for it to be considered long-term, but most folks agree 12-18 months is sufficient to satisfy the IRS that the property is an investment and not a flip (inventory).The opposite strategy involves converting a rental to a primary residence, so the process is essentially flipped in the beginning.

I've seen it dozens of times now, in articles from mainstream money magazines to tax advisor's websites, and the IRS pubs I've read seem to support it (although some pubs haven't been updated yet to reflect TCJA). 

I could realistically see my earned income double the next time I job hop, and could easily find similar employment if I was to lose my job.

Flipping activity will likely be challenged as ordinary income by the IRS under the theory that flipping is a real estate business rather than a passive investment.As per your question about extracting capital from your properties via mortgages or credit lines, it’s merely a question of cost, i.e., interest rate, points, and other fees, as well as terms.  

Once you have a deal under contract and proven that you're not just a tire kicker looking to get their hand held through a deal, I'm sure plenty of people on BP would be more than happy to answer specific questions whether it be on the forums or someone willing to hop on the phone with you for 15 minutes to give you some pointers on a specific questons.And lastly, don't underestimate the importance of actually getting out there and meeting people at meetups.

I've already gotten an EIN for the trust, but I'm really unclear on how I do his final taxes this year... the IRS site says I need to submit form 1041 for "trust-related income"... but what about the rest of his tax environment??