I'll check around with some lenders to see what they share about their comfort with the timeline - whether HELOC or not.  

For real estate just start analyzing as many deals as you can so you get more comfortable and confident.

The seller will always retain the equity and would receive annual distributions - and could structure the agreement with an exit strategy that makes them comfortable. 

Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

While great for cashflow, may limit your exit stratgy.Also, How comfortable are you with the offer as well as the overall numbers on whether this will or will not cash flow? 

But if you're comfortable with rougher areas, then you can definitely find properties at lower prices.

Meeting the material participation hours is absolutely doable, even with a property manager, as long as you stay actively involved in key tasks like marketing, bookings, and bookkeeping.

This helped me yesterday when someone inquired about a stay in October. 

Connect with a housing coordinator if that position is available in your area and stay in contact with that person. 

You don't want to lose your rate on the house you are living in now unless you want to sell it so since that is an owner-occupied, you need to stay there and save up the 20 percent for the second property based on what you said.