A bit risky, but it worked.Having said all the above, I did not have the complication of a mortgage on these properties because I used line of credit funding on my principle residence.  

I personally reel like it makes it more complicated. 

The tricky thing, these are people who were newish friends so that makes it complicated.

Are you worried that because the house was built in 1947 there may be complications in the rehab?

I've closed 2 complicated deals last month at lawyers and both fell apart.

This might work right now with 2 units but assuming you will grow this will get too complicated. 

Sorry in advanced if it's a long complicated post! 

So I've complicated your decision a bit here on what you should use the cash out net proceeds for....

Note the initial conversation with the lawyers does not cost money so you won't have to pay anything out of pocket and in the end if the property can be converted from a 1 to 2 or 3 family as a right of way, you may not even need a lawyer but these things can get complicated so you really want to make sure you get as much info as you can before you buy the property. 

If you receive rent the parking spaces you have complications.