I have a confession: my only duplex, which I gave owned now for 2 years and recently moved out of from a house hack, has proven to cost me more to maintain/pay taxes/repair/fix etc to the point where my cash flow is close to zero.

Yes, you will have to file the partnership tax return.

You want an investment that pays for itself, including mortgage, taxes, insurance, maintenance, and even some money set aside for a reserve to cover vacancies and capital expenditures.

I had to redo everything they did on my taxes. 

Eliminate debt, establish a budget, and save.

Salaries, compensation, rent, taxes, utilities, fees, MLS, etc.The flat fee model is a recipe for disaster."

People claim that 1031 investors over pay all the time just to avoid taxes.  

So obviously being in foreclosure, absentee owner, tax lien or any of such "distress" doesn't make you motivated.So what you need to ask yourself is "how do these software determine who or what is a motivated seller right?

This is obviously much better than $1,400 per month.On top of that, you will now get 2x the depreciation write-off so your taxes should go down.On top of that, you will now get 2x the appreciation when real estate price go up.On top of that, your tenants are helping you pay down the loan, initially at about $100/mo for both properties, which gradually gets better and better.On top of that, you now have more units so if one or two goes vacant, you have more renters covering the losses of the vacant units.If you want to keep these properties, I would do a cash-out refi and go buy more rental real estate.

It would/could be only 15% capital gains tax and yes you could/would deduct all selling costs including commissions and transfer taxes.