I will be at the mercy of them for the next year unfortunately, hopefully I have few maintenance issues, this will reduce the opportunities for them to up charge.  

Congrats on the success of your investments and earning your license.

1) cannot qualify for traditional financing2) fears appraisal will come in low3) fears buyer will back out so reduces contingency optionsnote for cash purchase I expect a significant discount.  

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?

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

Lots of new supply now with reduced demand.

Per the mutual agreement between the Lessor and the Tenant, the Lessor has agreed to reduce the monthly rent from $3,200 to $3,100, allowing the Tenant to repaint portions of the house at their own expense.

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.

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.

If you use Podio as it's designed to be used, it will streamline every thing you do--from managing leads, managing projects, reducing your internal email count, to making your internal communications more efficient because conversations (which otherwise might happen in email) happen "in context" -- of the client record in your CRM, the project, or whatever it is that you are discussing.