Hey @Michelle Baldwin, yes this is a challenge but everyone said it best.Simply, you can just use a different browser to be logged into each VRBO account.I also think that @John Underwoods idea will work as well.

I do have some very limited experience with commercial, but I've found it to be risky when retail vacancies come up, at least in the Bay Area.

NOTE: we charge extra for this.4) What about a floor plan, so prospective tenants can get an idea where their furniture may fit?

I'm not quite sure as i've never been in this situation before, just throwing an idea out there. 

Use three of those to give you an idea of what your property will sell for.Sometimes, I'll do a quick and dirty comparable analysis by averaging the value values from Zillow, Realtor, and Redfin.

Is there a limit to how high I can go? 

Being in the Army limits my ability to travel and explore markets firsthand.

If you want to be truly passive while living abroad you could consider a DST transfer or syndication where you transition your properties to professional management and get paid as a limited partner and not have to worry about any sort of property management takes.

Would a HELOC or home equity loan on my personal home be a good idea to fund this?  

He liked the idea so we created an LLC and a partnership agreement and he deposited 100k into the business account.