That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

Setting up direct bookings is a great way to save on fees, but you’re right—it requires extra effort to ensure everything runs smoothly.For vetting guests, start by asking a few questions when they inquire, like the purpose of their stay, how many people will be there, and if they’ve stayed in short-term rentals before.

Since most people who are not actively seeking a sale are not motivated to sell at anything other than a top of the line price, this is going to be a numbers game of x thousands of contacts for every potentially doable deal.  

As an example, we decided to replace the windows in a house we were renovating and ended up costing us $50,000 extra because we got into issues with permitting and suddenly found ourselves having to hire an architect, speciality contractors, etc.  

With the extra cash flow, you could strive to acquire additional income-producing properties over time.

In the case mortgage foreclosure, I usually offer to pay for the existing mortgage and give them a little extra to move.

Now where is that EXTRA dollar?

It's easy to obtain, costs very little, and doesn't require extra, on-going effort to maintain.

Also, keep in mind that an IN multi member LLC would require a separate tax return, so you would want to budget for extra admin fees.

If appreciation is slow and steady, and no extra liquidity is available, the basic fundamentals of personal finance do catch up to this investor.