Lack of reservesThe one enabler I would add to @shiloh lundahl advice is if you don't have sufficient reserves - partner with someone who does.

It will just take longer to accumulate a portfolio enabling you to retire. 

It wouldn't be a surprise that in nice neighborhoods almost every household would have a stable paycheck enabled by WFH. 

Tesla and Electrify America buildouts enable substantial coverage.

This enabled us to turn our old house into our second longterm rental.

Brookfield’s new fund, for example, purchased the two-thirds stake in mall giant GGP Inc. that Brookfield didn’t already own.Brookfield’s scale enables it to get returns “you simply can’t get if you’re an individual investor buying an individual mall,” said Brian Kingston, chief executive of Brookfield’s real-estate arm.Blackstone’s global co-head of real estate, Kenneth Caplan, who declined to comment on the fundraising, said markets are fickle and whether or not there are opportunities to buy “can change pretty quickly.”Some funds are setting less ambitious fundraising targets.

There's nothing in the Keating memo that would enable you to limit occupancy to one individual although you may be able to charge $XXXX for single occupancy and then an increase for any additional occupant with a limit of two per bedroom.

Find people who have skills and aptitudes that I don't, and enable their projects.BTW way I do kind of take exception to the idea that being over 40 or 50 is something that needs to be "admitted" rather than indicated.

Questions:-are there tax benefits that would enable us to save (write off/shelter) more $ if the rental property has a higher mortgage / value.

I think the sum up is that people gave you feedback that you didnt want to hear or deal with, and your agent  enabled this because they didnt want to rock the boat.