While I’m still in the early stages, I’m incredibly motivated to learn, grow, and surround myself with like-minded individuals who can help guide me along the way.What drew me to real estate is that I saw it as the best route for me and family to have financial freedom.

Whether its for investors, agents, or just a general meet up for like minded individuals .

When I partnered with friends on a multi-unit property a few years ago, we chose individual umbrella polcies from our personal providers.

My first choice would be a duplex but I'm also looking into single family.

There will likely be a partnership return required where you flipped a house with a partner and lost $120,000.If you sold the other property within the same partnership, it will also be reported on that partnership return.The net result to you is that you will receive a K-1 showing your income / loss which you then use to report on your individual return.If you made no money within the same year, you likely pay no additional taxes / get no additional refund.Best of luck.

I understand I can increase liability in each individual landlord policy, but one single umbrella policy is much more cost effective when I have multiple properties.

A mid-term rental could be an great option during the 6-7 months you're away since it appeals to traveling professionals, remote workers, or individuals relocating and offers stable income without the constant turnover of short-term rentals.

Does anyone know if this individual needs to be a W2 or can I hire on a 1099?

When an individual landlord prices their rental, they do based on what the other ones in the neighborhood have rented for. 

Well, of course it depends on the individual circumstances, the amount of time comitted and the capital available.