I would add the cost of initial repairs to your total cash assumption up front.  

I'm also curious why you think "hope is the most important part of my business plan" seems like a large assumption. 

I would be under the assumption I could get the same amount of rent plus more for my condo.

This will be a wall of text, but I've thought this through and hope someone can check my math and assumptions about how this works.My goal is to compare 15 years of real estate investment using a $60k base cash investment plus $12k injected personal cash per year.

Thanks for the feed back I was under the assumption you could only acquire one.

I'm definitely leaning toward turn-keys but I'm really struggling with either going with a better area (and more premium turn-key company) where it appears (at least on paper) that my CoC return after all expenses is 6%-8% (with the assumption that I will be able to "sleep better at night") versus going with a lower class area (and potentially a smaller and less reputable turn-key company) where my CoC return is 10%-12% (or higher). 

I am looking at an opportunity:Single Family, Ask price $44,900 (projected purchase price of $40,000)Taxes, $1,400Rent $867/month (rented with long term tenant)Assumptions:5% vacancy10% maintenance5% reserveOh this would also be 100% financed long term with a private mortgage at 4.5%My analyzing spread sheet conservatively shows a cash flow of $4,100/year or $344/month.I really am not sure I want to putt the trigger on this one....My first deal (duplex) is projected to cash flow at almost 6K/year and I really didn't want to look at anything under 5k.I am new to this, but am I crazy? 

My assumption is that its harder with wholesale because the houses are more likely to need some work - I could be off the mark on that, I've never explored buying wholesale properties.

I definitely agree with @Andreas Mirza In general, people who dream of house hacking in Orange County tend to make incorrect assumptions of their potential for cash flow.

Unless you can 100% tell there are no lintels, I would make the assumption that the builder who built the house put lintels in and look for additional reasons why they could be cracking.