But allocate the proceeds so that one of the purchases uses maximum leverage and other property uses minimal or no leverage. 

If this is a property that will just throw off cash for a long time with minimal improvement, then I'd want to invest for the long-term. 

I'd say minimally you need to be able to come up with 30K from whatever sources you can to make it work and that's even at 100% financing.

Ways to minimize repairs? 

Think about issue you will come across with renting, what kind of creative ideas can you come up with to prevent/minimize the damage/work in a pro-active manner to prevent these issues. 

If you find something that minimizes your expenses and would cash flow once you moved out, I would look twice.

Since it was fairly organized, it had the effect of minimizing the amount of trash we had to have hauled away.

If you bought a home with a mil to househack, your bottom line would likely be better than it would with the minimal cashflow from the current property if you kept it.  

If I were to offer higher than asking price to lock down the deal, the only thing that would change expense-wise would be my P+I, but that would be minimal. 

If they don't require the drawings to be Certified by a Licensed Architect, you can find someone with drafting/design knowledge to draw the plans for you for your submittal; however, when the Building Department reviews the drawings they will still want to ensure the proposal meets local Building Codes & Ordinances, or if they are the type of department that doesn't do thorough reviews, they could be leaving the liability to You in order to ensure the construction is safe & complies with codes.As a Licensed Architect myself, I recommend you consider the benefits of hiring a licensed professional, even if the building department doesn't require Stamped drawings; however, I realize that depending on how minimal the scope of work is, it may not provide you much additional benefit compared to finding a decent drafter at a lower cost...You may want to check out Upwork.com as well, theres a lot of posts on there for various architectural & drafting gigs all around the world.