Regarding the first scenario, the sale of the rental properties should be generating 'passive income'.If you have passive losses in the current year or from a prior year, you should be able to offset it against the passive income.

The city offers relatively affordable property prices compared to many other major markets, which can be great for getting good value and generating positive cash flow.

He is working with several other operators to categorize transactions, reconcile accounts, manage late payment collections, pay vendors, generate end-of-month statements, P&L reporting, and other bookkeeping tasks.Nonetheless, happy to make an intro.

@Kevin L. buy a home that you can improve and add value, including turning the garage into an ADU.Also, take the ugliest room and rent out the rest to generate income to offset the mortgage payment or to accrue cash for improvements or additional investments.

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? 

I just wish the energy would be more of a positive "lets build this industry together" approach vs. the alternate approach.

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.