Also of course I know it does mean holding back more money for repairs (two of everything, except for roof etc).

We're talking new roof, new electrical (wiring too, not just box), new AC, new kitchen with granite, stainless, porcelain at a diagonal, serious landscaping.

I priced out a roof replacement on an 8-unit building (4 upstairs, 4 downstairs) and I can get a new roof on an 8-unit apartment for the same cost as 3 SFHs.Scale is also a magic word along with Exit strategy. 

After the purchase, I spent 9.9K on a new roof and 1.3K on the AC system.

It may be hard to get good flooring at the cost at the lower end of your range, same with roofs if you are removing the old shingles and putting on a lifetime roof. 

Overhanging tree branchesHere are some additional things that you may want to gather on the property:The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated

Working on our due diligence phase now, I already know we need to replace the roof, so going to get some bids on that.

The lower priced one is similar to the rental I am looking at.The subdivision is 75% owners.This house will need a new roof in 3-4 years.

The NN leases could just be roof with a warranty transferable to buyer or it could be roof structure, utility lines, parking lot, etc.You mentioned a national dental chain.

. - Medium Rehab (Bathroom, Kitchen, Roof)$50/sq. ft. - Heavy Rehab (Full gut)  CONSTRUCTION$100 / sq. ft