Wondering about paying through an escrow agent or something similar 

The only extra pay for guests is the surf-rider.

While buying one that’s up and running might seem a good idea - paying for speed - if you’re not quite ready, sometimes the best deal you make is the one you don’t make at all.

Can pay cash but prefer to finance part of it How did you add value to the deal?

Once the property is sold we will be able to pay off the HELOC and will also have further funds coming in the following year.

You pay for what you get remember LOCATION , LOCATION! 

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.

Please see the rough numbers below :Tear down house price 350k,Construction cost 165 sqft * 2 build=627k too much for the land unless your exit is 3 million. don't reinvent the wheel. no single family home builder is paying 300k for land. that's miami florida prices where I live. we buy land 50k and under in Columbus Ohio. keep land at less than 10% of after built value.

While they mostly aren't lying, they leave out a lot of reality.Why would a government funded program like S8 pay MORE than market rents?

In effect, you will end up paying tax on your refi cash later on, when you sell the property.