However, for a new investor and landlord, it would seem a leap for me to think I can do better, or at least risk a negative cash flow monthly for this gamble.  

Most networking events with the big players happen in the daytime here and doing something as simple as delivering materials can offset a day or 2 of contractor work because I'm at the office#3 I love my tech job, but I'm not used to being comfortable for so long, its unnerving#4 I could try to change jobs to something that is more interesting, and could improve my negotiation/facilitation skills, but it would likely still not be my passion as much as real estate and training others...Plus it has more overtime potential (moving from programmer to business systems analyst would be my next career thought)#5 Realistically, I could only probably start out with 2 small deals with these funds and still have breathing room, and it would obviously be a gamble.

It will be a gamble either way, I just don't know which has the best chance for success. 

But one or the other needs to be done or you are gambling not investing.Also, recommend you understand the Iowa code as there may be an open redemption period.

I ended up gambling that we would close and did the majority of the repairs myself.Current rents on the home were $3,000 for the main house and $1,200 for the studio.

First off, not being able to inspect a property in depth is a huge gamble, one I would never consider taking personally.Secondly, those prices they are posting are advertisements, meaning that's what the auction will start off at, it goes up from there, and oh, does it go up quickly on a good looking property.

Also, the existing tenant quality varies and inherited tenants can be a gamble as you have not applied your own screening criteria or onboarding (in fact, existing tenants are not uncommonly part and parcel of why an owner is selling, due to payment or behavior issues)....Best of luck.

ITs much like those that buy 5k houses in the mid west and big inner cities and resell them to unsuspecting LA based investors or west coast or off shore investors for 40 to 80... claiming them to be cash flow investments....

but I guess $135 isn't a huge gamble.  

When you have neither, it is gambling.