My last job was with the American Red cross which i held for about 7 years.

While it has been relatively good in terms of rates of returns, the markets have been red hot and finding the same type of good cash flowing deals has been difficult for now. 

So things that are a red flag for me may be fine for someone more aggressive.1) Portfolio matching: (takes 30 seconds per deal)a) Have an educated opinion on where you think we are in the real estate cycles (financial and physical market cycles)b) Then only then pick the strategies, capital stack, and specialized asset subclasses that make sense for that opinion.

From what I can gather they are bringing in an income of over $30k+ per year before expenses.What kind of red flags should I look for with a beach rental?

First off two weeks from potential purchase and not knowing what a property manager would cost is a red flag in my opinion. 

The last situation I would want to be in is with a close knit group, where something goes awry and everyone involved in the deal thinks differently about what the outcome should be.And take it from me, when someone introduces themselves with a first and last name that isn't really their first and last name, let that send up a red flag. 

Other than the comps telling you bad news, are there any other particular red flags you look for specifically?

update.my 3 unit cash out was cancelled by quicken loans. i give them no stars.90 days and $500 later to tell me they dont accept reserve money in dba account. i needed 2 months in personal savings. this after 10 other stupid red tape bait switch tactics. and 3 different loan officers all with varying degrees of knowledge.

WP is red hot right now. 

So things that are red flag for me may be fine for someone more aggressive.1) Portfolio matching: (takes 30 seconds per deal)a) Have an educated opinion on where you think we are in the real estate cycles (financial and physical market cycles)b) Then only then pick the strategies, capital stack, and specialized asset subclasses that make sense for that opinion.