If we do a land contract and put $107,000 down after selling one maybe two building, net gain for us of (8) units.

Building (additions & alterations) - review your condo declarations and bylaws. 

The financial adviser that is establishing our lines of credit is charging 8% of the line of credit up front, with no additional payout to him thereafter.

And even if there were midterm rental management companies, I wonder if the increased commission they'd take for higher turnover would eat into any gains you get from the medium-term model. 

So after reestablishing 2 year primary residence status, if we were to decide the sell our home at this time, would the "nonqualifying use" apply to the capital gains? 

Hi Rose- Few things to note about buying an investment property.1) Expect to be putting down 25%, as this is most lender's required downpayment on "investment" properties.2) You likely won't be cashflow positive unless you are putting >50% down, OR are buying in a C-class or worse neighborhood.3) Starting out with a condo or townhouse could be a great idea if you're just looking to get your feet wet with landlording- It is less maintenance than SFH or MFH, and you will gain invaluable experience managing a tenant.Aside from the financial challenges, I think it's great that you have the mindset to grow your portfolio.

You can read the books in the BP bookstore and watch videos on YouTube and gain enough knowledge to get started and buy a small multi family house 2-4 units to house hack or just rent out and self manage.

Let's talk about Capital Gains Tax.

In addition, the "buyer" is the county sheriff so in essence, I'm fighting a battle with a local cop while I'm the outsider! 

Purchase price: $601,000 Cash invested: $450,000 Contributors: Jess Haas Rental Type: SFH(4bd) + ADU(2)Condition @ Purchase: Heavy FixerStrategy: Dormer Addition + ADU