And evaluating the track record is a call that's made first by the taxpayer or their CPA, and ultimately by an IRS auditor (should one get involved). it is very true that the IRS cares about intent with respect to capital gains in real estate -- I've certainly seen cases where the statutory timelines were less important and the identified intent of the investor.with respect to determining whether you qualify as a developer or an investor, it's much more of a "forest" than the "trees"...so holding any given investment for 14 months prior to a flip is certainly no guarantee of receiving long-term capital gains treatment.I hope this helps.  

While I look & wait for the next house hacking opportunity , I've identified identified Value add as the long term strategy I’m most interested in.I am looking to get started with Fix & Flips and also BRRRR to get experience with Rehabs with a focus on using OPM.

In order to get an insurable title, I have to submit a Quiet Title suit to county court, research to identify and notify possible claimants, and present the case to the judge. 

Many lessons learned, how to identify a stick built house and a manufactured house and that the appraiser is different for both types.When the property you buy is divided into 2 different townships, who takes care of what utility.

However, we now believe that exploring less competitive markets could potentially offer greater value for our investment.Would appreciate any mentorship or recommendations on websites to identify areas with the highest returns nationwide for multi-unit properties.

Your dad identified a path that worked well 15 years ago.

There is more nuance to this and not necessarily visible on a spreadsheet but those who are most succesful in real estate can identify these opporutnties. 

@Angie Hensley Most states require a lease to identify the owner of a leased property, whether a person, trust, LLC, IRA, etc.Landlord = Lord of the Land = Owner per deedAgent = someone legally representing the ownerProperty Manager = Agent

Make connections with nearby real estate brokers, investors, and property managers to get knowledge and expertise.Look for properties with capacity for appreciation, value-adding potential, and good cash flow possibilities when identifying investment options.

Even better is if you come to them with a personal financial statement, a debt schedule, and a business plan for the purchase (if you haven't identified a property, then what size, location, price you are looking for).