That’s always going to win in the end as to coming out ahead as long as you make smart financial investments (such as maintaining control of your own investments, and making smart choices on properties that cash flow, etc).  

That's hitting the 2% "rule", and if you can maintain regular rent on that you've really hit a home run in today's market.

I would expect start-up costs such as stocking linens/bedding, upgrading certain furnishing and amenities, and pass-through costs for listing on the OTAs (like VRBO, Airbnb). 

In today's world you need to be about 28-35% down on properties to be gross cash flow positive, closer to 40-42% to be truly net cash flow positive(i.e 50% of your income goes to maintaining the property, other 50% is actually profit).My recommendation is to buy ideally a 4/3 SFR that's a starter-friendly one in a good area, and rent it out by the room.

If they say put up higher railings, additional smoke detectors, etc, complete it promptly and document it.I've been in the landlord business for 20 years, and I've always kept my properties to code and well maintained. 

Our goal is to purchase two multifamily properties per year, and we want to ensure that we establish the most effective structure for asset protection from the outset.We’re exploring options such as Subsidiary LLCs, Parent LLCs, and Irrevocable Trusts to maintain both asset protection and anonymity.

Also Since you plan to live there for 3-5 years, it’s easier to manage and maintain, giving you time to learn the ropes of real estate.That said, be mindful of high HOA fees, as they can eat into your margins and affect future cash flow.

Utlimate goal is to maintain a healthy leverage on the rental property.

Any way to delay the official sale to keep taxes low while still maintaining a contract to buy? 

Investors buy shares and earn returns through dividends and potential stock price appreciation.You typically can’t lose more than your initial investment with publicly traded REITs.