The unobstructed water views for both front STR units can be challenging to determine additional value compared to other 3-unit properties without views.

I’ve had most luck with signs in front of my plaza and word of mouth - networking at Chamber of Commerce and chatting with other business owners in the area.

In this area MTR works well, also signing slightly longer term rentals for the school year and then doing a couple month long MTR for the summer has worked for me in the past.

However, I cannot be signed into both her account and my own VRBO for my 2 properties at the same time.

I'd say start the process of securing your HELOC if you havn't done so and spend time analyzing deals and determining what type of investor you are looking to be. 

This helps you determine what offer makes sense to you.

It's a great way to expand your real estate business if you can find individuals willing to co-sign.

What you should do is determine what story the house is already telling with its design and add onto it from there.

Those are probably the biggest questions someone needs to know to determine the feasibility of your ask.  

You need to learn how to analyze property and determine if they are a good investment.Here's a guide that describes how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...