You will typically receive lower rates than what you would see with a hard money lender. 

Would it be better to go for a lower end home and use a 203k loan to rehab and finance or get one that's not as bad off and start there?

Much lower price point for ours than yours and they aren’t lasting on the market.

Wages there will be lower, too.  

For a lower entry point, Thornton, Aurora and federal heights are good places to start. 

I'm from Massachusetts, and I'm specifically interested in land flipping, at least to start - the low barrier to entry, the simplicity (vs rentals), and ability to do it while working a full time job and being a dad makes it appealing to me. 

not a great deal compared to buying 5 year term first trust deeps on performing rentals that pay 9 and 10% and you get paid off in 6 months then what .. no return.. until you find another deal so your drag on money turns your return much lower.. now if it was 10% or 7k over 6 months that would be something to think about.. but not an interest rate for such a short duration.

My only concern would be a drop in the economy and not being able to cover costs in case I had to lower rent. 

Here in Chicago, the $1M+ SFH market starting really softening about a year and a half ago but for several months no one lowered prices.

Lower to market n you'll have a tenant by next week Thursday. 2.5 Months without rent is $5,000. $65 a day adds up fast.