Extra Income = Build or Purchase?

[Jake E.]

Hello there! I own some RE books and have taken some basic RE classes, but have never really jumped in. My wife is the business person & CPA, I am more on the artistic end of the stick. We own a 100 year old home which after 6 years I am finally almost done restoring. Its been a long, fun (sometimes not fun) process! It has taken me a while as I have a full time job (part owner) and on the side I run several online businesses that generate passive income. I am to the point where I would rather buy properties and rent them (or flip) to generate income instead of working with family members at my day job ;) ;) ;)

That said I am trying to hash out some ideas right now just to get my feet wet. Our goal is to move out of our main property (2ba/1ba) into a larger home, and then generate income other ways such as rentals or flips.

1) Our home is in an urban setting & zoned for additional rental units. I could probably fit in two more units and I have funds to build. Looking at comps I could probably get $1300-1500/m per unit, so $4000+/m total with current mortgage around $2300/m.

2) My other option would be to rent out our main house, and then purchase 2-4 small rental properties in a resort town 2 hours away and rent them year round.

Which options make sense? Thanks for any thoughts!

PS... Its possible I build only one extra unit on main property and get $1400 for that and $1700 for the front house. This would drop our monthly rental from $4000 to $3100, but still above our mortgage.
PPS... Im very handy and can renovate myself. 
PPPS... One of the reasons we have not already added on units to our main house is it feels expensive. In my area architects end up costing $20K-$30K when all is said and done. Seems like a lot and I want our funds to go as far as possible. I have 3 or 4 friends who own their own construction companies that I would like to work with and do my additions (and drawings) but they are all BUSY and are turning down smaller jobs like mine left and right.

Any thoughts or idea would be greatly appreciated! Thanks!