In both Denver and Colorado Springs, we had numerous clients in the last two years move here from San Francisco and Seattle to get a (slightly) more affordable home and enjoy the lifestyle that Colorado delivers (@Matt M.'

Also, hopefully there won't be too many obstacles, but if they are, make sure you can see a plan to circumvent them.Hidden costs in wholesaling is really perception. 

Including a separate "Tenant Rules & Regulations" (Brandon Turner provides a great one with his Book on Managing Rental Properties) can be a tremendous help in setting the perception that you're a professional landlord with your tenants.

$575K could get you a multi-family (or numerous multi-families, if not a small apartment complex) in some markets (not necessarily in Boston MA).

You are doing your 1st Duplex deal, house hacking and the numerous people on this board in some form or fashion tell you to take legal action, drop the transaction, don't honor the lease, and keep the less paying tenant.  

Kris Ashili - Define your rental criteria and apply evenly across all applicants.Example:- Credit score > 650, else cosigner needed - Proven income > 3x rent- No violent/sexual crime records- Good references from job & 2-3 previous landlords (this could let you legally deny them all if you found bad prior history)- No evictionsAdditionally:- Upfront payment (1st/last/1 month sec dep or whatever is max allowed by law)- All tenants must be named on leaseTo avoid any perception of discrimination, apply the standards and send rejection letter highlighting (use check box form letter?)

That's for a hip roof (higher waste than gable) with numerous valleys.

I listen to numerous real estate podcasts, including bigger pockets, and I have heard many "self help" or alacarte services that help landlords manage their properties themselves.

If you are an executive Costco Member, they have numerous lenders to choose from for only $275 loan fee!

Even if you assumed the same passive return for both options...15%...you would have to analyze and invest in numerous flips (say 15 or so) over the course of 7 years to get the same return as 1 longer term syndication investment.