You end up generating some cash flow in interim and purchase at the mutually agreed upon price in say 28-24 months.

I started my STR without a pool heater and added that after generating some cash flow, but again that really depends on the current condition.

Is it generational wealth, or potential cashflow, or diversifying your retirement? 

Are you required to generate income though? 

There's a lot of ways to lose on 2nds but there is also a lot of ways to generate solid returns and higher interest yields with this strategy.

Seasonal profits take a little more work here, but generate a much higher cashflow than SF's.

Duplexes, triplexes, or small apartment buildings allow you to generate more rental income while spreading the risk across multiple units.

As for the estimated income taxes, there’s no gain until I actually sell the house, at which point everything would be in COGS anyway—under your method or J Scott’s method—so I’ll know how much net income was generated and can easily estimate income taxes.

We dealt with rentals, flips, commercial, small apartment complex developments (~10 apartments), sport facilities, and a few government contracts.We are actually very open to different opportunities and investment approaches, but our plan was to start "smaller" with some cash deals in NJ (maybe somewhere in the area between Staten Island and Philadelphia, but staying in NJ), by flipping a few smaller properties and starting to generate some income.

Rent out any bedrooms you aren't using while you live there to generate even more cashflow.