I started by saving up for a down payment which was 5% for the first "second home" property in 2004, then 10% on the next few. 

Quote from @Mary Jo Carruthers: @Albert Hepp Did you know that there are quite a few non profits and also the city of Austin in the austin texas area that provide down payment assistance for first time home buyers?

I feel like it would be great to trust a property management company on all of this, but it would be hard not to step in if you could do a better job at screening bad tenants (eg screening HUGE future problems).I initially managed properties myself, but now I delegate that responsibility to my business partner, personal assistant, or a property manager at my brokerage.Most PMs I know will send you an applicant for final approval and you can get on the phone with them and ask them questions

I would offer it on a land contract to someone wanting to live there for around 1500 and small down payment or sub2 with a large down payment and monthly that would cover PITI.

Verify before you trust.

I have ZERO intention of making any payments on these contracts, nor do I want the equipment.

Following the shiny object, throwing money at a market you don't know well, and blindly trusting strangers that have a clear profit motive put you in a poor position to succeed regardless of where you choose to invest.

As lenders, well issue a prequal/preapproval letter if we've analyzed your income, assets (bank and brokerage statements to establish that you have the liquidity to afford the down payment, closing costs, and reserves), review credit of the guarantors, review the relevant experience to ensure that we're not throwing our money away on newbies that are wandering around in the dark, and have put together a reasonable plan of attack for the project.

Another question is… Which option would be better to cover the missing mortgage payments: a HELOC or forbearance?

Trust is made up of two things: Competence and Character.