You could do a selective cash out refinance on one property to give you tax free living cash.If you do sell you'll want to do a 1031 exchange if you can so that you can avoid tax on all of your gain. 

Knowledge is power and worst case you'll discover it's not a career you want to do but have a better understanding for how it all fits together. 

Here is my situation:- I'm a W2 employee that earns north of $500k a year- My wife is a stay-at-home-spouse- I'm looking to buy ~ $1,000,000 in STR Real Estate by the end of the year (as an investment and to offset my tax bill)I'm fairly well versed in the rules surrounding using STR to offset active income.

if the building cashflows really well ... it wouldn't be a big deal to use a loan for dp right...at 10% down for lower income housing I don't have much money and I think that this is the best way to get multi-family management experience to meet hud loan requirements in the future which Have the lowest Down payment options.Am I overthinking it?

Being that I have my own property and feel I have a lot of basic knowledge on Real Estate I wanted to make sure she is protected when she sells the property. 

I'm a "newbie" by definition with one duplex under my belt but would be interested in meeting up as well to share stories and explore opportunities.  

This really isn't a question of what's the "best" way to invest, it's more what works well for you, your resources and lifestyle. 

I'm also open to other markets as well.

When looking for an agent, I would make sure they have extensive market knowledge, and are able to help you run numbers on potential properties in the area.

Someone is going to buy and renovate the property; so, it may as well be you, someone who will handle it respectfully (and many residents end up staying).