Just because they have a season (or life) of financial struggle doesn't mean they can't handle other life affairs responsibly. 

Question to the seasoned investors: does that sound realistic?

@Jo-Ann Lapin I have to remind myself of those seasons and what expenses go along with them.

The last week of June thru the first week of Sept is the high season with a small shoulder season mid Sept thru Colombus Day.  

^^^^^^^^^^^^^^^^^^^^^^FOR STEVEN^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^Everyone;Newbies and seasoned investors and operators, there are four underlying factors of real property.

So let's say I need to put $10,000 in repairs over the next few weeks before El Niño (which scares the crap out of me, and I'm pretty sure will not be pretty for lots of people with older properties in SoCal...but that's a different story).  

So Brian you are not purchasing this property but the owner is older and just wants someone else to manage correct?

generally the older the properties the higher the fees due to the cost of maintenance rising property taxes etc Fees also increase over the years but they should be matched to a well kept property as @Nick Britton said read over all the condo docs and especially the budget paying attention to reserves,expenses etc .I have lived in the Palm Springs area for a number of years and have see condi fees as high as $1000 per month on some of the older properties.If you a re looking at a investment in this area it has a host of problems as you noticed,rising fees is a big one.

. , and using this money for the either down payment of 20% to purchase a $80,000 - $100,000 property that is an REO here in my area, which would give me a PITI of around $600 a month , and I can easily rent a property in this price range in my area for around $1,100 - $1,200 per month .... for a monthly cash flow of around $500 - $600 per month.I could then "Hopefully" do a No-Seasoning Cash-Out refi ( since I'll be purchasing the property as an Investor/Investment Property )....

Look for older homes being refreshed as you hit the pavement for your research.