An umbrella is usually a good idea but it's dependent on your personal situation. 

Purchase price: $68,000 Cash invested: $5,000 Sale price: $99,000 4 Unit quad in Medina NYRenters were tough and management company's locations are too far for a regular check up.Had a renter pass away and then DCS came in and the house was condemned due to farm animals in the upstairs unit where the person passed.We were too far to keep tabs on this investment so we sold the home.

The better performance of the others will “prop” up the total performance of the entire portfolio.

However, I applied to Furnishedfinder in person and listed the apartment as a sublease.

I've found that in my personal connections that simply sharing the information and being transparent has worked the best.

The drawings can go back and forth but the rater needs to be local to the property because in the end he will have to go verify what came out of the build and prepare a reconciliation showing the actual performance numbers post construction. 

I initially rented the home $150 less than similar homes at the time because the tenant was a "known" person and they could not pay more (at the time the tenant had a lower paying job than today), plus it was convenient for me to have someone mover right away.

I own 5 properties in Morningside personally and am closing on a duplex there next month.

I figured its a win win, they get to invest into some real-estate and grow their retirement as well as it will lighten my investment and potentially allow me to get into a better property that would cash flow/appreciate better.Does anyone have personal experiences or opinions on this?

It could very well be the route that is "cheapest" now, ends up being substantially more expensive down the road.If the costs above are not worth it to you...maybe pass on the LLC and get yourself a good insurance policy, and maybe an umbrella policy personally.