Was the owner doing his own repairs and hiding the costs?  

I will say REPS is one of the areas of the tax code where it is very costly to get wrong.

In Milwaukee, I'd need 2 exits from the attic and 50% of the space has to have at least a 7 foot height on ceilings.Two things you want to check: both requirements are correct, but on top of that the city is getting reluctant permitting 3rd units: 50% more occupants mean 50% more water and sewer and 50% more traffic and parking.The other issue is that the cost of finishing a thrid floor with proper insulation/ventilation will run about $50-60/sf and only makes sense if you can get strong rents. 

I am using a Heloc to fund my real-estate purchases and also to cover the rehab cost. 1.

Why would he prefer a $1500/mo (150k-purchase cost) 2 BR 2 BA 1000 SF condo over a $250k 4 BR 2-3BA 2000 SF house where we rent out half and live for like $500/mo?

Understanding How Real Property Works I am not making the argument to do anything unsafe or that you need to do all of the work on your properties yourself but I believe that understanding how real property works will save you from being ripped off, allow you to prioritize repairs more effectively, and get you out of tough situations by providing you with solutions to problems.Why Basic Home Maintenance Skills MatterCost Savings: Knowing how to do some basic things yourself can save thousands of dollars.

What's the cost?

Get caught with your pants down on paper first, it costs less. 

I would look at the effectiveness of what you do, not the nonsense the oddball responder spews.

If you are in the actual SubTo community, there is no way they haven't been spam calling you and grouping you so you should have access to that inside of the Facebook page or paid groups.But, seconding @John Clark, if you are new as an investor, choosing SubTo is going to cost you a lot and get you a little.