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Paypal...fast and easy!!

I second PayPal

Are you sure that the property manager is actually maintaining the property?
If the checks are being returned and they were not returned previously, maybe they are no longer at that location?
If they have not been payed in a while because the checks have not reached, they are not likely taking care of your property.

I am not sure why you were using Cashier checks and not regular checks, regular checks can be deposited in a bank and are just as good.

Getting to the point, I wonder if you are not being taken for a ride, if you are actually getting value for your hard earned money.

If they insist on PayPal, Western Union money transfer or Cashier Checks, it sounds like they are working under the table and may not be doing what you expect. Sorry but I am a little short on Trust when there are conditions like that and or no contracts.

You may want to call friends to check your place out and see if the maintenance company is still at that address.

Thank you.  PayPal was what I was hoping to hear! 

The contractor is VERY TRUSTWORTHY, no worries there, but thanks for your concern.  The problem is NOT with him, it is with Western Union and the post office delivery.  We did not send him checks in the past, it was just a last resort consideration.  We sent drawings to him for an addition on our property and they have all come back to us, even though he swears it is the correct address and he receives mail from other senders at the exact same address.  Relatives nearby as well as renters weekly confirm the property is well-maintained!

Paypal, US Post Office Money Order, Domestic wire transfer.

That is good to know all is well with the maintenance!

Get a debit card from Walmart you can deposit up to 2000 for $4 dls send the card to PR you deposit the money at Walmart anytime you want for four dls each time, it is cheaper and very efficient. The price better than Western Union. The person in PR can go to cooperativas up to 500 a day for $1.50  cooperativa de Ahorro y Credito Rincon, Mayaguez, etc

Problems with delivering mail, I suggest you get a PO Box for 6 months for around $35 dls

We used to pay our contractor by bank transfer directly into his account. You can transfer up to $2K a week that way.