Information and experience you gain from a knowledgeable and experience mentor can be a totally different story.I think there's much more value in the right mentorship. 

All of the units are currently rented.I plan on raising the total rent to $3400 (it is currently under priced)I plan on putting $5-10k into rehab At the $271k price I’m looking at an estimated -$26 cashflow loss while my wife and I are living there and a $355cashflow gain when we leave.$391 doesn’t seem like much so I may put one or two units on AirBnb.

For example, my plan is to focus on three passive income sources 1) real estate, 2) stock market cap gains and dividends, and 3) online business models such as blogging or Amazon FBA.

Better to build your own equity through the debt pay down, enjoy the tax benefits of ownership, and garner the equity of an appreciating asset.

They would have way more benefits than doing a sandwich lease.

So, they will want to know that you are serious and in it for the long haul before they start giving you equity in the deal.Honestly, if I was in your position as a new investor with no experience who found an experienced investor to partner with, I would be less focused on how much money I will get paid in the short-term and more so on how I will use the experience I gain to make exponentially more $ in the future. 

Many cities already have taxes on hotel income (9.5% in Baltimore), so the short-term income tax seems fair even though many hotels get other benefits and tax breaks from many cities.

My intention is to grow an organic scaffold that can be of benefit to my community and I believe real estate investment will be my conduit for that eventuality.

Should we sell my wifes house and make $80k-100K now(it would close after April 2019 to avoid capital gains) to reinvest later?

I would worry about the potentially much higher interest rates though.Regarding the tax implications, since we have lived here long than 2 years, I don't believe short term capital gains tax would be applicable at least.