He traded property that he was tired of managing that he paid 20k for that is loosing value plus 100k in cash.

What is the best way to go about raising the rate to create more cash flow without loosing tenants?

Much like "any" professional you are bound to get different answers, including out here.

Do you guys think that I am being too conservative or are others just being too loose with their money?

In a small number of those cases you may loose a bit of money evicting someone that would have otherwise paid most of the rent but it will pencil out to a higher profit margin over the long term.

As part of the settlement many large banks did in fact get bound to take what Fannie/Freddie was offering and  Fannie and Freddie agreed to standardize short sale processing as a result as well. 

We did not loose much money but it sold for a lot less than some of the property tax valuations and the RE took a lot or time (overseeing the repairs from 2 hurricanes).I still love the location of the property and may go back there to vacation but as an RE investment it did not work for us. 

Taxes, HOA, insurance etc are bound to be different in different markets!

I would also be bound by certain rules imposed by the local real estate board.

Lately we have had many leaking and loose toilets.