For reference I own exactly one handful (5) SFH  rentals in my hometown, all have been purchased in the last 4 years.1) buying at a discount is MY preferred way to reduce risk.

All else being equal, lower mortgage rates reduce the cost of ownership and, thereby, allow more people to afford to buy.

-As far as trying to sell land with no access, sometimes I've sold those to neighbors who want to increase their acreage, or utility companies, cities or other public entities who could use the piece for whatever reason.

Most Buyers don't even know that there is a public access portal to search local listings.

I recommend people doing a side gig on what they specialize in.I am an accountant and when I worked within large public accounting firms, I had a side gig of bieng an accountant.I had a salary with my employer so regardless of how much more hours I put with them, i would be paid the same. 

With that in mind, which approach do you think works best:1.Use property management software (PMS) as an intermediary to automate payments and fee splits while reducing legal risk and simplifying operations?

These expenses can create a paper loss, which may offset other passive income or carry forward to future years.If you qualify for Real Estate Professional Status (REPS) or actively manage a Short-Term Rental (STR), the losses can be applied against your active W-2 or business income, reducing your overall tax liability.

I'm not 100% committed either way between the income benefits of multifamily vs. the reduced headaches of SFH tenants.

I don't believe that will change as long as the school system and public safety levels remain some of the worst in the state.

Using your first property as collateral could help reduce the cash you need upfront, but it’s essential to weigh the risks and it's not really recommended specially if this will be your first.I recommend focusing on building reserves or seeking partnerships to fund flips.