Take someone along with you as a witness.If you are concerned and have a carry permit you are fine otherwise find a witness that has a carry permit to go along.

The monthly expenses would be around 3,400/mo So subtracting the rents on both original houses leaves me with a $800/mo mortgage on the third new home which I'd live in with my father and split all costs making it extremely affordable for both of us.

After taxes, mortgages, and expenses, I am clearing about $700/month.I am concerned because at the end of the day, any property can be a cash flowing property if enough money is put down.

If the $ is big enough it might make sense to consult with an attorney to determine if this was handled properly by the seller/condo association as concerns prospective purchasers.

It's extremely frustrating to go weeks into the process and receive the low offer. 

Any help finding potential buyers would be extremely appreciated (plus, of course, you would have a free stay at our gorgeous hotel when you visit Portugal!

@Ryan Blake I agree with you to some extent however in @Manasa Srinath case I don’t think she should be overly concerned about the apartments. 

Once a year I get a call from a "concerned" neighbor about the "language" used by a tenant or contractor - usually complaining about "the F word" (why does no one call to complain about "the S word"??). 

They are extremely hungry, super friendly, knowledgeable and will wrap up your mortgage insanely fast.

It also concerns me that the majority of your STR market is golfers, I am looking for something that has the potential for year round rental potential.