This mostly affects low priced houses under 100k, but it's something to note. 

A payment history of at least one year is much more attractive to investors than zero payment history. having the Bene and the Trustor being he same entity or closing related is something most knowledgeable investors simply would not do.I have seen a few of those on FCI  usually in low value asset land its just another way to sell the property.. 

As a rental, even on the low side, figuring $2,000/mo for a $100k investment in Greenwich, ain't too shabby IMO. 

Off street parking, low maintenance, open floor plan on main level, central-air, fenced rear yard.

Sometimes your risk reward changes substantially with the types of projects you can get into for one vs the other.As some other posters have alluded to, time constraints drive a lot - a light rehab/cosmetic buy and hold is possible for navigating while having a 'regular' job - and certainly managing rentals while working is possible as well.The last one, and I'm surprised no one has mentioned this - is market specific. 

I anticipate that if I sold, I could probably get on the low side $500K and on the upside maybe $550K/$600K.

Now the tax assessments can vary widely, I’ve seen land value as low as 3% and as high as 65%!

The reason for the seller's willingness to discount that much in today's climate, from what info I have so far, is due to the extremely low rate on the modified loan (less than 2%, recast for a new 30 year term).So due to the rate, even at 50% of UPB, the return on my investment would be around 4% after considering servicing fees, etc., which is not nearly enough to interest me in this deal, considering the risks of borrower re-default, etc. 

You'll probably need to go with a low down payment program like FHA. 

We are also losing out to cash offers since our price point is low (under $150,000 in south Florida).