We are in VERY difficult economic times and I am seeing people group together with increasing frequency so that they can afford the rent.

I'll probably start with calling slightly more frequently than once a week until I see that things are moving and then reduce the frequency.

@Joseph Felder one investors I now kept a radio scanner tuned to the fire dept frequency.

You transfer or share the risk using the insurance for the expense that is HIGH in Severity and Low in Frequency(see below).

I have been doing it for about 2-3 months and have gotten a few deals from it, but I am trying to increase that frequency (obviously).

It does after all add a very difficult problem to the matter, which is the timing/competition of the offers, and the frequency of offers not accepted (especially when competing with people uninformed and offering top dollar).

Don't just waive late fees... it frequency sets a precedent and you will see an increase in late payments and requests to cut them a break. 

Perhaps I will consider increasing the frequency of my mailers as well.Is there a certain services you are using to skip-trace the numbers  for your leads?

There should be some form of regular interest payments that are similar in frequency and rate to what your brother should expect if he were to go to an unrelated party in the open marketplace.   

I'll give a little different take....in my experience once you have a legal lease that you're happy with you may never encounter another legal question ever.The tax issues important in terms of frequency because you'll face them every year and taxes are likely your #1 expense beside mortgage interest.The 2 main keys to being successful are that if something breaks, you fix it for the tenant and the tenant has to pay the rent on time.