The extra cost to do two separate loans will be worth it, especially if you do not want to be stuck with the loan for a long time. 

Living in one unit and renting out the others could offset a significant portion of your mortgage, giving you extra breathing room as the sole income earner.

It’s all about what will draw guests in and make them choose your listing over others.2️⃣ Standout Amenities: Rentals that offer something extra, like a hot tub, game room, or eye-catching design, often attract more bookings and higher rates.

After adding an extra bedroom and bathroom and rehabbing the house, I was well over budget.

Requiring occupant to have renters insurance is another possibility for extra protection.

Well, STR can work well for people who own a vacation house for personal use, and just want to generate some extra income when not in use.  

I looked into the maintenance option years back to discover a trend of:  apx. 8% monthly fee which only included rent collection (everything else from maintenance to turnovers etc, extra, and poor reputation on repairs.)

I think the big question is how badly do you want to keep the extra $50k liquid?

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

You are not paying for their services and won't cost you anything extra anyways.