Investing is different from speculating, in that it’s data driven and therefor predictable and you have factors that play in that covers your downside and strengthen your chance of upside. 

If your property manager is not listed as an additional insured, they may not be covered under your policy in the event of an incident on your property, leaving both of you potentially exposed to liability.It can save you money.If your property manager is not added to your insurance policy as an additional insured, they may be forced to purchase their insurance policy to protect themselves.

The main factor is will rents cover the debt liability and can you sustain 3-4 months of no income to cover the debt? 

I have umbrella insurance under my personal names currently so I'm wondering if the umbrella insurance would cover me in the event of some liabilityQuestions:- Am I better off keeping the rentals in my name since I have umbrella insurance?

Switching the utilities into their name without safeguards in place—knowing the tenant might act out—seems like a misstep on their part.While it’s true you’ll ultimately have to cover the cost, it doesn’t feel entirely fair for you to shoulder the consequence of their decision.

One of the things we do and recommend to our clients is to purchase a home owners warranty to cover all of the mechanical, electrical and plumbing compenents.

Verify credit, employment, etc for you. 6) I would definitely want noise (quiet hours), guests, and treatment of common areas covered. 7) We've used Rent Manager as it focuses more on the financials which I think is super important.

By adopting the house-hacking method—living in one unit while renting out the others—we plan for the tenants to cover the mortgage and gain valuable property management experience.

Another option is to explore private lenders or HELOCs to cover the equity.

As noted, if your options are Reg D, private offering vs fully registered public offering, even if you are talking Pink Sheet (OTC) stocks, you have public filing costs, annual audit requirements, and likely more on-going expenses that have to be covered by the property(s) owned by the offering.