As others are noting, it's important to run your numbers and would probably only recommending pulling from the HELOC for short term opportunities.

There is still plenty of room above how much the mortgage is.Honesty and trust are important and it seems you're not getting that.

There are some great tax strategies for short-term rentals, but very important to be aware of the personal use rules to make sure 280(A) doesn't become an issue. 

I think being diversified is important for a variety of reasons and can allow you to take other risks.

All you get is what you can export/import via CSV file:(We use Propertyware, have experience with Buildium, and have played with Appfolio and RentManager.Buildium is for smaller companies.The other three are tied, the differences being how much automation & customization you want to do.If you don't see yourself growing beyond 150 units, go with Buildium.If you're not very techy and plan to grow over 150 units, we'd recommend Appfolio.If you're techy and plan to grow over 150 units, we'd recommend Propertyware or RentManager.Of course, schedule some demos, take GREAT notes and them make your decision.FYI - there are MANY new options on the market, RentRedi, TenantCloud, Apartments.com, Hemlane, Rentec.

The sewer main is one of the most important, and most valuable parts of the property...so, why wouldn't we inspect that too?

Important things to check include opening and closing every cabinet, looking under sinks, pushing on doors and cabinets, and checking commonly used areas.

I guess tourism is an important enough industry there that while they need to limit the short term rentals for local residents, they also need them to provide lower price points for visitors. 

It is important to consult with a real estate agent with knowledge of how panels affect your properties value.

Could you expand more on what other things are important to you in this investment?