I attribute my ability to invest “remotely” in SFHs to a team of people I’ve gathered over the years that look out for my best interests; primarily an excellent real estate agent and an outstanding property manager. 

In a performing market, it's human nature to attribute our gains to savvy investing (rather than overall trend) and to  thus over-allocate due to inflated confidence.  

typically cash.. but as has happened for this investor he was able to get financing.I attribute that to :1. his dad lives there so they have a local presense2. strong PG  strong credit and income3. some history in owning rentals not their first rodeo4.

I bought my first property at 28 and am now 32 (and 3 weeks)We are closing next week on properties 19 - 21 and I would attribute a large part of our success to having well paid corporate jobs and living well below our means.  

That might be your greatest attribute. 

I want lots of thriving economic attributes that support areas I invest in specifically.

On top of this, I house hack so I only attribute a percentage of the dwelling as eligible for depreciation. 

Just an idea, perhaps he should calculate the losses attributable to depreciation across all 15 years and hope the losses sustained during the early years (i.e., the years closed due to statute) were all suspended under the passive loss rules so they could carryforward into the present, so when he sells the property those losses are released to offset gain (e.g., gain attributable to full depreciation recapture which it sounds as if he will have no choice but to recognize).

As you are building a place, an expenditure is attributable to the enlargement of the building or the internal structural framework of the building is not as Qualified improvement Property. 

He still earned $2000 for posting an ad on Craigslist...And avoided a seize and desist order for brokering from the Dept of Real Estate (if he is not licensed)See http://www.dllr.state.md.us/license/mrec/mrecdodon...An unlicensed person MAY NOT:Prepare promotional materials or ads without the review and approval of licensee and supervising broker.Show property.Answer any questions on listings, title, financing, closing, etc.Discuss or explain a contract, listing, lease, agreement, or other real estate document with anyone outside the brokerage.Be paid on the basis of real estate activity, such as a percentage of commission, or any amount based on listings, sales, etc.Negotiate or agree to any commission, commission split, management fee, or referral fee on behalf of a licensee.Discuss the attributes or amenities of a property, under any circumstances, with a prospective purchaser or lessee.Discuss the terms and conditions of the real property offered for sale or lease with the owner of the property.Collect, receive, or hold deposit monies, rent, other monies, or anything else of value received from the owner or lessee of the real property or from a prospective purchaser or lessee.Provide owners of real property or prospective purchasers or lessees with any advice, recommendations, or suggestions as to the sale, purchase, exchange, or lease of real property to be listed or real property presently available for sale or for lease.Hold himself or herself out in any manner, orally or in writing, as being licensed or affiliated with a particular company or real estate broker as a licensee.Contact the public concerning the availability of real estate brokerage services unless an inquiry about a specific property is immediately referred to a licensee.Elizabeth H.