My theory is that the risk of losing the $100 just doesn't outweigh the cost of getting title insurance and going the traditional route. 

I believe there is a tipping point after you acquire a certain amount of units, where the risk of losing your job does not outweigh the benefits of "coming out" and being open about your REI.

OK Everyone I'm in a little bit of a conundrum and I think personal feeling may be outweighing the business side so I need some help from a outside opinionI have 4 rental properties all showing a good return in less than ten years they will be payed off and showing much better,the wife and I are tinkering with the idea of moving out of state, and we have a great property manager available that would be extremely cost effective. we currently use him-on one property to " try him out "We currently have a FHA loan on a 30 year 27 left 3.5%currently payout 950a month that includes taxes and insurance and a pmi that will falloff in two years lowering the note but about 150.although once we don't live there we will loose homeowners exemption thous increasing the note by roughly what the pmi drops.insurance will however be lower because we would drop it to the commercial policy that we have the other rentals in instead of a personal dwelling policy.its in a b- area up the street from the high school and 1 block from the historic district.two bedroom duplex's next door get $750 a month.rent in that area isn't extremely high so I am figuring a rent of $1250 after property management fees thus netting a 300 return before any repairs. recently upgraded the inside so hopefully that wouldn't be a issue for a few years but you never know.my question is would it be worth keeping?

Either of these could potentially save you money, so long as the cost of the fees to get the new loan don't outweigh any gains you would make.2) a "cash out refi" might make your payments higher  -- in fact it is likely that it will.

@Jerome Harrod IIThe answer your broker gave you sums up my feelings on it.The juice doesn't outweigh the squeeze."

Of course, it would be better if you didn't have to sink 200 - 400K into the downtown condo in the first place.If you want better cash flow and less cash up-front, you are going to have to venture a little further afield.Sound like you are about 2-years into your 5yr mortgage term  - and, at 3%, you went fixed-rate - which means the penalty to break the mortgage likely outweighs the benefit of refinancing (currently you should be able to get 2.5 ... or lower if you would entertain a variable rate mortgage).  

It seems the time cost of your/or your painters time to paint them would outweigh any savings over replacing them.  

Credit, income and job stability far outweigh anything else.

There are a few downsides (mostly the time and energy to get licensed, along with continuing education and a few costs up front and ongoing, and you need to disclose this to potential sellers), but most seem to agree that benefits outweigh the costs.

But feel that the investment potential of real estate outweighs the % interest on our loans, so its a fine balancing act.